Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials.

[1]  I. Fairlamb Asymmetric cycloisomerization of 1,6- and 1,7-enynes by transition-metal catalysts. , 2004, Angewandte Chemie.

[2]  Dinuclear zinc catalyzed asymmetric spirannulation reaction: an umpolung strategy for formation of α-alkylated-α-hydroxyoxindoles. , 2012, Organic letters.

[3]  Y. Rao Chemistry of Butenolides , 1964 .

[4]  A. Zheng,et al.  Insights into the dual activation mechanism involving bifunctional cinchona alkaloid thiourea organocatalysts: an NMR and DFT study. , 2012, The Journal of organic chemistry.

[5]  M. Shi,et al.  The application of chiral phosphine-Schiff base type ligands in silver(I)-catalyzed asymmetric vinylogous Mannich reaction of aldimines with trimethylsiloxyfuran , 2009 .

[6]  J. Pedro,et al.  Highly enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides catalyzed by Cu(II)-BOX complexes. , 2011, Organic letters.

[7]  H. Tao,et al.  Catalytic Asymmetric Cascade Vinylogous Mukaiyama 1,6-Michael/Michael Addition of 2-Silyloxyfurans with Azoalkenes: Direct Approach to Fused Butyrolactones. , 2015, Journal of the American Chemical Society.

[8]  B. Wirz,et al.  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety , 2011 .

[9]  Lili Lin,et al.  Asymmetric Direct Vinylogous Aldol Reaction of Unactivated γ-Butenolide to Aldehydes. , 2010 .

[10]  B. Lipshutz Rediscovering OrganocopperChemistry Through Copper Hydride. It’s All Aboutthe Ligand , 2009 .

[11]  S. Denmark,et al.  Catalytic, enantioselective, vinylogous aldol reactions. , 2005, Angewandte Chemie.

[12]  P. Mueller,et al.  High enantioselectivity in the intramolecular cyclopropanation of allyl diazoacetates using a novel rhodium(II) catalyst , 1991 .

[13]  Z. Wang,et al.  Asymmetric Baeyer-Villiger Oxidation of 2,3-and 2,3,4-Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H2O2 as the Oxidant , 2011 .

[14]  H. Ikeda,et al.  Avenolide, a Streptomyces hormone controlling antibiotic production in Streptomyces avermitilis , 2011, Proceedings of the National Academy of Sciences.

[15]  jin-quan yu,et al.  Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity. , 2009, Chemical Society reviews.

[16]  C. Bolm,et al.  Catalytic, asymmetric synthesis of phosphonic γ-(hydroxyalkyl)butenolides with contiguous quaternary and tertiary stereogenic centers. , 2014, Chemistry.

[17]  Jinxing Ye,et al.  Diastereodivergent organocatalytic asymmetric vinylogous Michael reactions , 2014, Nature Communications.

[18]  R. Bandichhor,et al.  Paraconic Acids: The Natural Products from Lichen Symbiont , 2005 .

[19]  T. Baba,et al.  Asymmetric Michael addition reactions of 2-silyloxyfurans catalyzed by binaphthyldiimine-Ni(II) complexes. , 2004, Chemical communications.

[20]  Zhiyan Huang,et al.  Weak arene C-H···O hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones. , 2013, Angewandte Chemie.

[21]  B. Foxman,et al.  Asymmetric vinylogous aldol reaction of silyloxy furans with a chiral organic salt. , 2010, Journal of the American Chemical Society.

[22]  Davidr . Evans,et al.  C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Catalytic Enantioselective Aldol Additions of Silylketene Acetals to (Benzyloxy)acetaldehyde , 1996 .

[23]  Chen Yang,et al.  Mechanism and selectivity of bioinspired cinchona alkaloid derivatives catalyzed asymmetric olefin isomerization: a computational study. , 2013, Journal of the American Chemical Society.

[24]  B. Feringa,et al.  Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis. , 2011, Organic letters.

[25]  M. Struchkova,et al.  A concise synthesis of highly enantiomerically enriched 2-alkylparaconic acid esters via ruthenium-catalyzed asymmetric hydrogenation of acylsuccinates , 2009 .

[26]  P. Mueller,et al.  Diastereocontrol for Highly Enantioselective Carbon-Hydrogen Insertion Reactions of Cycloalkyl Diazoacetates , 1994 .

[27]  P. Andersson,et al.  Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes. , 2012, Chemistry.

[28]  F. Wang,et al.  Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine. , 2004, The Journal of organic chemistry.

[29]  Lin Peng,et al.  Direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(5H)-one with aldimine catalyzed by quinine. , 2012, The Journal of organic chemistry.

[30]  Lili Lin,et al.  Highly enantioselective synthesis of γ-substituted butenolides via the vinylogous Mukaiyama-Michael reaction catalyzed by a chiral scandium(III)-N,N'-dioxide complex. , 2011, Organic & biomolecular chemistry.

[31]  C. Goodman,et al.  Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters. , 2012, Journal of the American Chemical Society.

[32]  J. Młynarski,et al.  General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents. , 2012, Chemical communications.

[33]  V. M. Dong,et al.  Enantioselective ketone hydroacylation using Noyori's transfer hydrogenation catalyst. , 2013, Journal of the American Chemical Society.

[34]  Choon‐Hong Tan,et al.  Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions. , 2012, Angewandte Chemie.

[35]  P. Kočovský,et al.  Enantioselective Baeyer-Villiger oxidation catalyzed by palladium(II) complexes with chiral P,N-ligands. , 2008, The Journal of organic chemistry.

[36]  C. Bolm,et al.  Copper- and vanadium-catalyzed asymmetric oxidations , 1997 .

[37]  Y. Matsumura,et al.  New efficient organic activators for highly enantioselective reduction of aromatic ketones by trichlorosilane. , 2006, Organic letters.

[38]  K. Krohn,et al.  Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus Xylaria sp. , 2004 .

[39]  Yunlong Guo,et al.  Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides , 2013 .

[40]  R. Rossi,et al.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides. , 2010, Chemical reviews.

[41]  H. Yanai Green and catalytic methods for γ-lactone synthesis , 2021, Green Synthetic Approaches for Biologically Relevant Heterocycles.

[42]  M. Elsegood,et al.  An asymmetric synthesis of trans-fused butyrolactones from endoperoxides. , 2013, The Journal of organic chemistry.

[43]  Xumu Zhang,et al.  Highly Enantioselective Cyclocarbonylation of Allylic Alcohols Catalyzed by Novel Pd-1,4-bisphosphine Complexes , 1999 .

[44]  K. Scheidt,et al.  Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates. , 2010, Journal of the American Chemical Society.

[45]  S. Mukherjee,et al.  Remarkable influence of secondary catalyst site on enantioselective desymmetrization of cyclopentenedione , 2014 .

[46]  S. P. Fletcher,et al.  Current methods for asymmetric halogenation of olefins. , 2011, Chemistry.

[47]  M. Krische,et al.  Regio- and stereoselective construction of gamma-butenolides through phosphine-catalyzed substitution of Morita-Baylis-Hillman acetates: an organocatalytic allylic alkylation. , 2004, Angewandte Chemie.

[48]  S. Buchwald,et al.  Enantioselective functionalization of radical intermediates in redox catalysis: copper-catalyzed asymmetric oxytrifluoromethylation of alkenes. , 2013, Angewandte Chemie.

[49]  J. Carretero,et al.  Catalytic asymmetric vinylogous mannich reaction of N-(2-thienyl)sulfonylimines. , 2008, Organic letters.

[50]  A. Charette,et al.  Stereoselective cyclopropanation reactions. , 2003, Chemical reviews.

[51]  S. Amslinger,et al.  Asymmetric synthesis of both enantiomers of arteludovicinolide A. , 2013, Organic letters.

[52]  T. Montagnon,et al.  Using singlet oxygen to synthesize polyoxygenated natural products from furans. , 2008, Accounts of chemical research.

[53]  M. Sawamura,et al.  Asymmetric Hydrosilylation of Keto Esters Catalyzed by a Rhodium Complex with Trans-Chelating Chiral Diphosphine EtTRAP , 1995 .

[54]  T. Akiyama,et al.  Vinylogous Mannich‐Type Reaction Catalyzed by an Iodine‐Substituted Chiral Phosphoric Acid , 2008 .

[55]  Ryan P. Wurz Chiral dialkylaminopyridine catalysts in asymmetric synthesis. , 2007, Chemical reviews.

[56]  T. Katsuki,et al.  Highly Enantioselective Cr(salen)-catalyzed Reaction of 2-(Trimethylsilyloxy)furan and Aldehydes. Effect of Alcohol on Enantioselectivity , 2003 .

[57]  J. McLaughlin,et al.  Annonaceous acetogenins: recent progress. , 1999, Journal of natural products.

[58]  A. Yanagisawa,et al.  Catalytic enantioselective synthesis of chiral γ-butyrolactones. , 2011, Organic letters.

[59]  B. Feringa,et al.  Palladium catalyzed stereospecific allylic substitution of 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one by alcohols , 1999 .

[60]  D. Enders,et al.  Enantioselective synthesis of α-alkylidene-γ-butyrolactones: intramolecular Rauhut-Currier reaction promoted by acid/base organocatalysts. , 2012, Angewandte Chemie.

[61]  T. Katsuki,et al.  Enantioselective Addition of 2-(Trimethylsilyloxy)furan to Aldehydes Using Cr(salen) as Catalyst. Effect of Water on Enantioselectivity , 2003 .

[62]  T. Hashimoto,et al.  A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization. , 2016, Journal of the American Chemical Society.

[63]  Emily C. Gentry,et al.  Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation. , 2012, Journal of the American Chemical Society.

[64]  I. Nakamura,et al.  Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis , 2004 .

[65]  S. Martin,et al.  Vinylogous Mannich reactions. Catalytic, asymmetric additions of triisopropylsilyloxyfurans to aldimines , 1999 .

[66]  T. Pilati,et al.  Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes , 2004 .

[67]  R. Rios Organocatalytic enantioselective methodologies using Morita–Baylis–Hillman carbonates and acetates , 2012 .

[68]  B. Figadère,et al.  Highly Enantioselective Aldol Reaction with 2‐Trimethylsilyloxyfuran: The First Catalytic Asymmetric Autoinductive Aldol Reaction , 2000 .

[69]  C. Bolm,et al.  Enantioselective Baeyer-Villiger Oxidations Catalyzed by Chiral Magnesium Complexes , 2002 .

[70]  Charles H. Martin,et al.  (R)-3,5-diCF3-SYNPHOS and (R)-p-CF3-SYNPHOS, electron-poor diphosphines for efficient room temperature Rh-catalyzed asymmetric conjugate addition of arylboronic acids. , 2011, Organic letters.

[71]  E. Talbot,et al.  Catalytic asymmetric synthesis of (+)-anthecotulide using enyne and Meyer-Schuster rearrangements. , 2011, Organic letters.

[72]  A. Alexakis,et al.  Highly enantioselective organocascade intermolecular iminium/enamine Michael addition on enals. , 2011, Chemical communications.

[73]  S. You,et al.  Stereoselective Synthesis of γ‐Butyrolactones via Organocatalytic Annulations of Enals and Keto Esters , 2008 .

[74]  B. Feringa,et al.  Synthesis of enantiomerically pure γ-(menthyloxy)butenolides and (R)- and (S)-2-methyl-1,4-butanediol , 1989 .

[75]  Xumu Zhang,et al.  New Chiral Phosphorus Ligands for Enantioselective Hydrogenation , 2003 .

[76]  J. Bode,et al.  N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes. , 2004, Journal of the American Chemical Society.

[77]  Y. Yeung,et al.  Organocatalytic EnantioselectiveHalolactonizations: Strategies of Halogen Activation , 2011 .

[78]  Lili Lin,et al.  Catalytic asymmetric vinylogous Mannich-type (AVM) reaction of nonactivated α-angelica lactone. , 2011, Organic letters.

[79]  B. Figadère,et al.  Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes: Application to Muricatacin Synthesis , 1998 .

[80]  M. Boiocchi,et al.  Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes. , 2012, Chemistry.

[81]  M. Mihovilovic,et al.  Enantioselective Baeyer-Villiger Oxidations , 2004 .

[82]  Yong Wang,et al.  Synthetic Study of Rubriflordilactone B: Highly Stereoselective Construction of the C-5-epi ABCDE Ring System. , 2016, Organic letters.

[83]  M. Doyle,et al.  Comparative evaluation of enantiocontrol for intramolecular cyclopropanation of diazoacetates with chiral CuI, RhII and RuII catalysts , 1997 .

[84]  K. C. Kumar,et al.  Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism. , 1999, Journal of natural products.

[85]  M. Doyle,et al.  Enhancement of enantiocontrol/diastereocontrol in catalytic intramolecular cyclopropanation and carbon-hydrogen insertion reactions of diazoacetates with Rh2(4S-MPPIM)4 , 1995 .

[86]  Zhenyuan Miao,et al.  Asymmetric Aldol Reactions of Heterocyclic Dienolsilanes and α,β-Unsaturated Carbonyl Derived Dienolsilanes , 2012, Synthesis.

[87]  R. K. Boeckman,et al.  Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: application to a total synthesis of (-)-rasfonin. , 2006, Journal of the American Chemical Society.

[88]  D. Pratt,et al.  A Continuous Visible Light Spectrophotometric Approach To Accurately Determine the Reactivity of Radical-Trapping Antioxidants. , 2016, The Journal of organic chemistry.

[89]  C. Pinel,et al.  (R,R) dipamp-ruthenium (II) (2-methylallyl)2 : Synthesis and selected use in asymmetric hydrogenation. , 1992 .

[90]  B. List,et al.  Kinetic resolution of homoaldols via catalytic asymmetric transacetalization. , 2010, Journal of the American Chemical Society.

[91]  S. Denmark,et al.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective. , 2012, Angewandte Chemie.

[92]  C. Bolm,et al.  Ligand effects in aluminium-catalyzed asymmetric Baeyer–Villiger reactions , 2006 .

[93]  C. Guillou,et al.  Synthesis of γ-butenolides and α,β-unsaturated γ-butyrolactams by addition of vinylogous nucleophiles to Michael acceptors , 2014 .

[94]  L. Wojtas,et al.  Highly asymmetric intramolecular cyclopropanation of acceptor-substituted diazoacetates by Co(II)-based metalloradical catalysis: iterative approach for development of new-generation catalysts. , 2011, Journal of the American Chemical Society.

[95]  R. Sheldon,et al.  The Baeyer-Villiger reaction: new developments toward greener procedures. , 2004, Chemical reviews.

[96]  J. Kangasjärvi,et al.  Populus euphratica Displays Apoplastic Sodium Accumulation, Osmotic Adjustment by Decreases in Calcium and Soluble Carbohydrates, and Develops Leaf Succulence under Salt Stress1[W] , 2005, Plant Physiology.

[97]  Hiroki Mandai,et al.  Three-component Ag-catalyzed enantioselective vinylogous mannich and Aza-Diels-Alder reactions with alkyl-substituted aldehydes. , 2008, Journal of the American Chemical Society.

[98]  M. Lautens,et al.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. , 2003, Chemical reviews.

[99]  K. Maruoka,et al.  Asymmetric Synthesis of α‐Acyl‐γ‐butyrolactones Possessing All‐Carbon Quaternary Stereocenters by Phase‐Transfer‐Catalyzed Alkylation , 2006 .

[100]  C. Bolm,et al.  Enantioselective Metal-catalyzed Baeyer-Villiger Oxidation of Cyclobutanones , 1997 .

[101]  M. Shi,et al.  Axially Chiral Phosphine‐Oxazoline Ligands in Silver(I)‐ Catalyzed Asymmetric Mannich Reaction of Aldimines with Trimethylsiloxyfuran , 2009 .

[102]  T. Rovis,et al.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes. , 2012, Advanced synthesis & catalysis.

[103]  O. G. Mancheño,et al.  H‐Donor Anion Acceptor Organocatalysis—The Ionic Electrophile Activation Approach , 2012 .

[104]  A. Alexakis,et al.  Highly enantioselective direct vinylogous Michael addition of γ-butenolide to enals. , 2011, Organic letters.

[105]  M. Snapper,et al.  A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions. , 2006, Angewandte Chemie.

[106]  T. Uchida,et al.  Highly Enantioselective Baeyer—Villiger Oxidation Using Zr(salen) Complex as Catalyst. , 2002 .

[107]  R. Noyori,et al.  Asymmetric hydrogenation of unsaturated carboxylic acids catalyzed by BINAP-ruthenium(II) complexes , 1987 .

[108]  E. Jacobsen,et al.  Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis. , 2011, Journal of the American Chemical Society.

[109]  F Zanardi,et al.  The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver. , 2000, Chemical reviews.

[110]  K. Asano,et al.  Asymmetric isomerization of ω-hydroxy-α,β-unsaturated thioesters into β-mercaptolactones by a bifunctional aminothiourea catalyst. , 2014, Organic letters.

[111]  M. Ogasawara,et al.  Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters , 1999 .

[112]  C. Bolm,et al.  C1-symmetric aminosulfoximines in copper-catalyzed asymmetric vinylogous Mukaiyama aldol reactions. , 2010, Chemistry.

[113]  S. Snyder,et al.  Halonium‐Induced Cyclization Reactions , 2012 .

[114]  M. Doyle,et al.  Chiral catalyst controlled diastereoselection and regioselection in intramolecular carbon-hydrogen insertion reactions of diazoacetates , 1996 .

[115]  T. Rovis,et al.  Exploiting Acyl and Enol Azolium Intermediates via N-Heterocyclic Carbene-Catalyzed Reactions of α-Reducible Aldehydes. , 2012 .

[116]  T. Ohta,et al.  Asymmetric Hydrogenation of Olefins with Aprotic Oxygen Functionalities Catalyzed by BINAP-Ru(II) Complexes , 1995 .

[117]  S. Schaus,et al.  Highly diastereoselective asymmetric Mannich reactions of 1,3-dicarbonyls with acyl imines. , 2006, Organic letters.

[118]  W. M. Davis,et al.  Preparation, crystal structure analysis, and catalytic application of [(S)-BINAP]Ni(COD) and [(S)-BINAP]NiBr2 , 2002 .

[119]  Rosaria Villano,et al.  Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system , 2006 .

[120]  Y. Yeung,et al.  Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst. , 2012, Chemical communications.

[121]  M. Shi,et al.  Highly Diastereo‐ and Enantioselective Vinylogous Mannich Reactions of Fluorinated Aldimines with Siloxyfurans , 2011 .

[122]  P. Norrby,et al.  Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): isolation, analysis and alkylation of the monomeric form of the cationic eta(3)-cyclohexenyl complex [(eta(3)-c-C6H9)Pd(TSL)]+. , 2009, Journal of the American Chemical Society.

[123]  M. Krische,et al.  Enantioselective Conversion of Primary Alcohols to α-exo-Methylene γ-Butyrolactones via Iridium-Catalyzed C—C Bond-Forming Transfer Hydrogenation: 2-(Alkoxycarbonyl)allylation. , 2013 .

[124]  B. Trost,et al.  The direct catalytic asymmetric aldol reaction. , 2010, Chemical Society reviews.

[125]  J. Robichaud,et al.  Formal enantioselective synthesis of (+)-compactin. , 2006, Organic letters.

[126]  T. Dohi,et al.  Asymmetric dearomatizing spirolactonization of naphthols catalyzed by spirobiindane-based chiral hypervalent iodine species. , 2013, Journal of the American Chemical Society.

[127]  O. Reiser,et al.  Synthetic approaches towards structurally diverse γ-butyrolactone natural-product-like compounds , 2005 .

[128]  S. Liras,et al.  Highly Selective Enantiomer Differentiation in Intramolecular Cyclopropanation Reactions of Racemic Secondary Allylic Diazoacetates. , 1996 .

[129]  B. Lipshutz,et al.  Asymmetric 1,4-Hydrosilylations of α,β-Unsaturated Esters , 2004 .

[130]  C. Bolm,et al.  Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones , 2001 .

[131]  B. Trost,et al.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. , 2003, Chemical reviews.

[132]  K. Tatsuta,et al.  Asymmetric Vinylogous Mukaiyama Aldol Reactions Using Vinylketene N,O-Acetals in Total Syntheses of Natural Products , 2008 .

[133]  K. Nakanishi,et al.  The stereochemistry of the grayanotoxins , 1962 .

[134]  Wei Zhang,et al.  Catalytic asymmetric dearomatization reactions. , 2012, Angewandte Chemie.

[135]  Sunit Hazra,et al.  Asymmetric syntheses of (-)-enterolactone and (7'R)-7'-hydroxyenterolactone via organocatalyzed aldol reaction. , 2009, Journal of Organic Chemistry.

[136]  F. Glorius,et al.  Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones , 2004 .

[137]  H. Ikeda,et al.  Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis , 2011, The Journal of Antibiotics.

[138]  S. Martin,et al.  Enantioselective conjugate addition employing 2-heteroaryl titanates and zinc reagents. , 2009, Organic letters.

[139]  A. Paju,et al.  Asymmetric Baeyer-Villiger Oxidation of Cyclobutanones. , 1996 .

[140]  P. Pihko,et al.  Mukaiyama-Michael reactions with acrolein and methacrolein: a catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins. , 2012, Organic letters.

[141]  T. Dohi,et al.  A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols. , 2008, Angewandte Chemie.

[142]  Chi‐Huey Wong,et al.  The Catalytic Asymmetric Aldol Reaction , 2000 .

[143]  M. Doyle,et al.  Asymmetric synthesis of lactones with high enantioselectivity by intramolecular carbon-hydrogen insertion reactions of alkyl diazoacetates catalyzed by chiral rhodium(II) carboxamides , 1991 .

[144]  S. V. Pansare,et al.  Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: application of an organocatalytic direct vinylogous aldol reaction. , 2012, Organic & biomolecular chemistry.

[145]  S. V. Pansare,et al.  Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes. , 2011, Chemical communications.

[146]  T. Kramer,et al.  Metallated 2-alkenyl carbamates: chiral homoenolate reagents for asymmetric synthesis , 1990 .

[147]  R. Brueckner The -elimination route to stereodefined ?-alkylidenebutenolides , 2001 .

[148]  J. Tedrow,et al.  Synthesis of 2-deoxyxylolactone from glycerol derivatives via highly enantioselective carbon-hydrogen insertion reactions , 1994 .

[149]  Chao Fang,et al.  Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst. , 2012, Organic letters.

[150]  S. Ye,et al.  Highly diastereo- and enantioselective NHC-catalyzed [3+2] annulation of enals and isatins. , 2011, Chemical communications.

[151]  B. Lipshutz Rediscovering Organocopper Chemistry Through Copper Hydride. It′s All About the Ligand , 2009 .

[152]  M. Oestreich,et al.  Polishing a diamond in the rough: "Cu--H" catalysis with silanes. , 2007, Angewandte Chemie.

[153]  Ke-Fang Yang,et al.  New silver(I)–monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction , 2013 .

[154]  Li Wu,et al.  Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. , 2010, Organic letters.

[155]  Lei Zhou,et al.  Catalytic carbene insertion into C-H bonds. , 2010, Chemical reviews.

[156]  J. Genêt,et al.  Potassium organotrifluoroborates: new perspectives in organic synthesis. , 2008, Chemical reviews.

[157]  L. Deng,et al.  Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule. , 2011, Journal of the American Chemical Society.

[158]  K. Bhat,et al.  Arglabin: From isolation to antitumor evaluation. , 2015, Chemico-biological interactions.

[159]  Tasuku Ito,et al.  SYNTHESIS OF 2,2′-BIS(DIPHENYLPHOSPHINO)-1,1′-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF α-(ACYLAMINO)ACRYLIC ACIDS , 1981 .

[160]  S. Ma,et al.  Enantioselective halocyclization reactions for the synthesis of chiral cyclic compounds. , 2010, Angewandte Chemie.

[161]  H. Alper,et al.  The First Stereoselective Palladium-Catalyzed Cyclocarbonylation of β,γ-Substituted Allylic Alcohols , 1997 .

[162]  O. Kitagawa,et al.  Iodocarbocyclization and Iodoaminocyclization Reactions Mediated by a Metallic Reagent , 1999 .

[163]  B. Stoltz,et al.  Palladium-catalyzed, asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones with PHOX ligands , 2011 .

[164]  Goutam Brahmachari,et al.  Green Synthetic Approaches for Biologically Relevant Heterocycles , 2015 .

[165]  D. MacMillan,et al.  Cycle-specific organocascade catalysis: application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis. , 2009, Angewandte Chemie.

[166]  Roman. Davis,et al.  Highly diastereo- and enantioselective catalytic synthesis of the bis-tetrahydrofuran alcohol of Brecanavir and Darunavir , 2008 .

[167]  K. Jørgensen,et al.  Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism. , 2004, Organic & biomolecular chemistry.

[168]  Yasunori Yamamoto,et al.  Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes , 2007 .

[169]  J. Rabe,et al.  Synthesis and Biological Activity of α‐Methylene‐γ‐butyrolactones , 1985 .

[170]  T. Katsuki,et al.  A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates , 1997 .

[171]  W. Drury,et al.  Design of chiral ligands for asymmetric catalysis: from C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[172]  Chenguang Yu,et al.  Diastereo- and enantioselective organocatalytic direct conjugate addition of gamma-butenolide to chalcones. , 2010, Chemistry, an Asian journal.

[173]  A. Chan,et al.  Highly enantioselective copper-catalyzed 1,4-conjugate addition of diethylzinc to cyclic enones and α, β-unsaturated lactones , 2004 .

[174]  G. C. Fu,et al.  Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile. , 2003, Journal of the American Chemical Society.

[175]  J. Kwiatkowski,et al.  The direct asymmetric vinylogous aldol reaction of furanones with α-ketoesters: access to chiral γ-butenolides and glycerol derivatives. , 2011, Angewandte Chemie.

[176]  P. Toullec,et al.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights. , 2008, Angewandte Chemie.

[177]  Can Li,et al.  The synthesis of chiral isotetronic acids with amphiphilic imidazole/pyrrolidine catalysts assembled in oil-in-water emulsion droplets. , 2012, Angewandte Chemie.

[178]  B. List,et al.  Asymmetric counteranion-directed catalysis: concept, definition, and applications. , 2013, Angewandte Chemie.

[179]  N. Kumagai,et al.  Direct catalytic asymmetric vinylogous Mannich-type reaction of γ-butenolides with ketimines. , 2013, Angewandte Chemie.

[180]  M. Shiro,et al.  Catalytic asymmetric iodocarbocyclization reaction , 1995 .

[181]  S. Martin,et al.  Synthesis and properties of cyclopropane-derived peptidomimetics. , 2006, Accounts of chemical research.

[182]  P. Kreitmeier,et al.  Cobalt(II)-Azabis(oxazoline)-Catalyzed Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds , 2005 .

[183]  Y. Hamashima,et al.  Catalytic desymmetrization of cyclohexadienes by asymmetric bromolactonization. , 2012, Organic letters.

[184]  M. Shi,et al.  Diastereo- and Enantioselective Construction of γ-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita–Baylis–Hillman Acetates , 2011 .

[185]  B. List,et al.  Catalytic asymmetric transacetalization. , 2010, Journal of the American Chemical Society.

[186]  J. Kampf,et al.  Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon. , 2006, Journal of the American Chemical Society.

[187]  G. C. Fu Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles. , 2000, Accounts of chemical research.

[188]  B. Borhan,et al.  An organocatalytic asymmetric chlorolactonization. , 2010, Journal of the American Chemical Society.

[189]  A. Mortreux,et al.  Asymmetric Hydrogenation of 2,4‐Dioxo Esters: Selective Synthesis of 2‐Hydroxy‐4‐oxo Esters and Direct Access to Chiral 2‐Hydroxy‐4‐butyrolactones , 1999 .

[190]  M. Shi,et al.  Chiral phosphine-catalyzed enantioselective construction of gamma-butenolides through substitution of Morita-Baylis-Hillman acetates with 2-trimethylsilyloxy furan. , 2008, Journal of the American Chemical Society.

[191]  T. Uchida,et al.  Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: stereospecific synthesis of abnormal and normal lactones. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[192]  Y. Funahashi,et al.  Cinchona alkaloid amide/copper(II) catalyzed diastereo- and enantioselective vinylogous Mannich reaction of ketimines with siloxyfurans. , 2013, Angewandte Chemie.

[193]  M. Shi,et al.  Chiral Phosphine-Catalyzed Enantioselective Construction of γ-Butenolides Through Substitution of Morita—Baylis—Hillman Acetates with 2-Trimethylsilyloxy Furan. , 2008 .

[194]  C. Bolm Metal‐catalyzed asymmetric oxidations , 1999, Medicinal research reviews.

[195]  Y. Zhang,et al.  Recent advances in organocatalytic asymmetric Michael reactions , 2012 .

[196]  J. Tedrow,et al.  Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates. , 1999, The Journal of organic chemistry.

[197]  S. Liras,et al.  Enantioselective Intramolecular Cyclopropanations of Allylic and Homoallylic Diazoacetates and Diazoacetamides Using Chiral Dirhodium(II) Carboxamide Catalysts , 1995 .

[198]  M. Terada,et al.  Enantioselective direct vinylogous Michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base. , 2011, Organic letters.

[199]  Tamio Hayashi Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient Olefins , 2001 .

[200]  Yong Huang,et al.  Enantioselective organo-cascade catalysis. , 2005, Journal of the American Chemical Society.

[201]  J. L. Gleason,et al.  Catalytic enantioselective homoaldol reactions using binol titanium(IV) fluoride catalysts , 2003 .

[202]  Scott J. Miller,et al.  Nucleophilic chiral amines as catalysts in asymmetric synthesis. , 2003, Chemical reviews.

[203]  G. S. Singh,et al.  Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks. , 2012, Chemical reviews.

[204]  T. Katsuki,et al.  A short-step synthesis of trans-whisky lactone by an asymmetric Michael reaction , 1998 .

[205]  Lili Lin,et al.  Asymmetric direct vinylogous aldol reaction of unactivated gamma-butenolide to aldehydes. , 2010, The Journal of organic chemistry.

[206]  T. Katsuki,et al.  Asymmetric Baeyer—Villiger Oxidation of Prochiral Cyclobutanones Using a Chiral Cationic Palladium(II) 2‐(Phosphinophenyl)pyridine Complex as Catalyst. , 2003 .

[207]  B. Borhan,et al.  On the chlorenium source in the asymmetric chlorolactonization reaction. , 2011, Organic letters.

[208]  Ying‐Chun Chen,et al.  Asymmetric assembly of 2-oxindole and α-angelica lactone units to construct vicinal quaternary chiral centers. , 2012, Chemical communications.

[209]  M. Doyle,et al.  Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones , 1996 .

[210]  Sean P. Brown,et al.  The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched gamma-butenolide architecture. , 2003, Journal of the American Chemical Society.

[211]  S. Matsunaga,et al.  Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis. , 2008, Organic letters.

[212]  Davidr . Evans,et al.  C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of the Catalytic Enantioselective Aldol Additions of Enolsilanes to Pyruvate Esters , 1999 .

[213]  K. Jørgensen,et al.  Catalytic asymmetric homo-aldol reaction of pyruvate—a chiral Lewis acid catalyst that mimics aldolase enzymes , 2000 .

[214]  Jipan Yu,et al.  Enantio‐ and Diastereoselective Vinylogous Mukaiyama Aldol Reactions of α‐Keto Phosphonates with 2‐(Trimethylsilyloxy)‐ furan Catalyzed by Bis(oxazoline)‐Copper Complexes , 2013 .

[215]  C. Deutsch,et al.  CuH-catalyzed reactions. , 2008, Chemical reviews.

[216]  Takao Saito,et al.  Developments in asymmetric hydrogenation from an industrial perspective. , 2007, Accounts of chemical research.

[217]  A. Sudalai,et al.  A NEW AND SHORT ENANTIOSELECTIVE SYNTHESIS OF (R)-PANTOLACTONE , 1999 .

[218]  Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5-cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride. , 2005, Organic letters.

[219]  N. Kumagai,et al.  Direct catalytic asymmetric vinylogous conjugate addition of unsaturated butyrolactones to α,β-unsaturated thioamides. , 2014, Angewandte Chemie.

[220]  Z. Wang,et al.  Charge‐Transfer Effect on Chiral Phosphoric Acid Catalyzed Asymmetric Baeyer‐Villiger Oxidation of 3‐Substituted Cyclobutanones Using 30% Aqueous H2O2 as the Oxidant , 2010 .

[221]  B. Trost,et al.  Asymmetric Transition Metal‐Catalyzed Allylic Alkylations , 1996 .

[222]  C. Poulter,et al.  Macrocyclic lactones from dirhodium(II)-catalyzed intramolecular cyclopropanation and carbon-hydrogen insertion , 1995 .

[223]  R. Zimmer,et al.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. , 2003, Chemical reviews.

[224]  Ying‐Chun Chen,et al.  Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts. , 2012, Chemical Society reviews.

[225]  Isamu Shiina,et al.  Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst. , 2013, Organic letters.

[226]  M. Krische,et al.  Regio‐ and Stereoselective Construction of γ‐Butenolides Through Phosphine‐Catalyzed Substitution of Morita—Baylis—Hillman Acetates: An Organocatalytic Allylic Alkylation. , 2005 .

[227]  C. Bolm,et al.  Optically Active Lactones from a Baeyer–Villiger‐Type Metal‐Catalyzed Oxidation with Molecular Oxygen , 1994 .

[228]  B. Feringa,et al.  Lipase-catalyzed second-order asymmetric transformations as resolution and synthesis strategies for chiral 5-(acyloxy)-2(5H)-furanone and pyrrolinone synthons , 1996 .

[229]  S. Gil,et al.  Recent Developments in γ-Lactone Synthesis , 2009 .

[230]  T. Uchida,et al.  Cationic Co(III)(salen)-catalyzed enantioselective Baeyer-Villiger oxidation of 3-arylcyclobutanones using hydrogen peroxide as a terminal oxidant , 2001 .

[231]  N. Kornblum,et al.  THE BASE CATALYZED DECOMPOSITION OF A DIALKYL PEROXIDE , 1951 .

[232]  A. Pfaltz,et al.  PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis , 2000 .

[233]  P. Sgarbossa,et al.  Catalytic asymmetric Baeyer-Villiger oxidation in water by using Pt(II) catalysts and hydrogen peroxide: supramolecular control of enantioselectivity. , 2009, Chemistry.

[234]  E. Negishi,et al.  Regio- and stereoselective synthesis of ?-alkylidenebutenolides and related compounds , 1997 .

[235]  Depeng Zhao,et al.  Development of metal/organo catalytic systems for direct vinylogous Michael reactions to build chiral γ,γ-disubstituted butenolides. , 2013, Chemistry.

[236]  D. Alonso,et al.  Organocatalytic asymmetric conjugate additions , 2007 .

[237]  E. Olhava,et al.  Total synthesis of (+)-azaspiracid-1. Part II: synthesis of the EFGHI sulfone and completion of the synthesis. , 2007, Angewandte Chemie.

[238]  R. Hocquemiller,et al.  Synthesis and structure determination of iso-cladospolide B , 2001 .

[239]  Davidr . Evans,et al.  A general method for the enantioselective synthesis of pantolactone derivatives. , 2002, Organic letters.

[240]  C. Bolm,et al.  Vaulted Biaryls: Efficient Ligands for the Aluminum-Catalyzed Asymmetric Baeyer-Villiger Reaction , 2004 .

[241]  M. Doyle,et al.  Total synthesis of (S)-(+)-imperanene. Effective use of regio- and enantioselective intramolecular carbon-hydrogen insertion reactions catalyzed by chiral dirhodium(II) carboxamidates. , 2002, The Journal of organic chemistry.

[242]  S. Saaby,et al.  The first catalytic highly enantioselective alkylation of ketimines--a novel approach to optically active quaternary alpha-amino acids. , 2003, Chemistry.

[243]  David C. Forbes,et al.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations. , 1998, Chemical reviews.

[244]  B. Trost,et al.  Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis. , 2009, Journal of the American Chemical Society.

[245]  P. Retailleau,et al.  Catalytic enantioselective vinylogous Mukaiyama-Michael addition of 2-silyloxyfurans to cyclic unsaturated oxo esters. , 2013, The Journal of organic chemistry.

[246]  Xinmiao Liang,et al.  Asymmetric Vinylogous Michael Reaction of α,β-Unsaturated Aldehyde with Buteno-4-lactone , 2011 .

[247]  T. Uchida,et al.  ChemInform Abstract: Highly Enantioselective Baeyer-Villiger Oxidation Using Zr(salen) Complex as Catalyst. , 2002 .

[248]  Gloria Rassu,et al.  The vinylogous aldol and related addition reactions: ten years of progress. , 2011, Chemical reviews.

[249]  S. Arseniyadis,et al.  Palladium-catalyzed asymmetric allylic alkylation of cyclic dienol carbonates: efficient route to enantioenriched γ-butenolides bearing an all-carbon α-quaternary stereogenic center. , 2013, Angewandte Chemie.

[250]  B. Trost,et al.  Palladium catalyzed kinetic and dynamic kinetic asymmetric transformations of gamma-acyloxybutenolides. Enantioselective total synthesis of (+)-Aflatoxin B1 and B2a. , 2003, Journal of the American Chemical Society.

[251]  George Bullard,et al.  Facile synthesis of versatile enantioenriched α-substituted hydroxy esters through a Brønsted acid catalyzed kinetic resolution. , 2013, Organic letters.

[252]  Recent Advances in Asymmetric Organocatalytic 1,4‐Conjugate Additions , 2007 .

[253]  T. Akiyama,et al.  Chiral Brønsted acid catalyzed enantioselective Mannich-type reaction. , 2007, Journal of the American Chemical Society.

[254]  E. Corey,et al.  Broad-spectrum enantioselective diels-alder catalysis by chiral, cationic oxazaborolidines. , 2002, Journal of the American Chemical Society.

[255]  M. Fushimi,et al.  Design of a small-molecule catalyst using intramolecular cation-pi interactions for enantioselective Diels-Alder and Mukaiyama-Michael reactions: L-DOPA-derived monopeptide.Cu(II) complex. , 2006, Organic letters.

[256]  Q. Zhang,et al.  Palladium(II)-catalyzed asymmetric cyclization of (Z)-4'-acetoxy-2'-butenyl 2-alkynoates. Role of nitrogen-containing ligands in palladium(II)-mediated reactions. , 2001, The Journal of organic chemistry.

[257]  A. Carnell,et al.  Chemoenzymatic synthesis and application of bicyclo[2.2.2]octadiene ligands: increased efficiency in rhodium-catalyzed asymmetric conjugate additions by electronic tuning. , 2010, Angewandte Chemie.

[258]  Wing-Yiu Yu,et al.  A novel palladium-catalyzed asymmetric cyclocarbonylation of allylic alcohols to γ-butyrolactones , 2006 .

[259]  D. Basavaiah,et al.  Recent contributions from the Baylis-Hillman reaction to organic chemistry. , 2010, Chemical reviews.

[260]  M. Shi,et al.  Axially chiral phosphine―oxazoline ligands in the silver(I)-catalyzed asymmetric Mannich reaction of fluorinated aldimines with trimethylsiloxyfuran , 2010 .

[261]  D. Basavaiah,et al.  Recent Contributions from the Baylis—Hillman Reaction to Organic Chemistry , 2011 .

[262]  C. Frost,et al.  Synthetic applications of rhodium catalysed conjugate addition. , 2010, Chemical Society reviews.

[263]  F. Costantino,et al.  A highly enantioselective one-pot synthesis of spirolactones by an organocatalyzed Michael addition/cyclization sequence. , 2011, Angewandte Chemie.

[264]  S. V. Pansare,et al.  Enantioselective synthesis of (S)-homocitric acid lactone and (R)-per-homocitric acid lactone involving organocatalysis , 2010 .

[265]  Yi‐Ru Chen,et al.  Organocatalytic enantioselective direct vinylogous Michael addition of γ-substituted butenolides to 3-aroyl acrylates and 1,2-diaroylethylenes. , 2013, Chemistry.

[266]  M. Braun,et al.  Tsuji-trost allylic alkylation with ketone enolates. , 2006, Angewandte Chemie.

[267]  M. Krische,et al.  Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation. , 2012, Journal of the American Chemical Society.

[268]  A. Hoveyda,et al.  Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: preparation of air-stable and catalytically active Cu-peptide complexes. , 2005, Angewandte Chemie.

[269]  T. Katsuki,et al.  Chiral Lewis Acid Promoted Asymmetric Michael Addition Reaction of 2-(Trimethylsilyloxy)furans , 1997 .

[270]  M. Yoshimura,et al.  Desymmetric hydrogenation of a meso-cyclic acid anhydride toward biotin synthesis , 2011 .

[271]  H. Alper,et al.  The First Stereoselective Palladium‐Catalyzed Cyclocarbonylation of β,γ‐Substituted Allylic Alcohols. , 1998 .

[272]  Y. Imada,et al.  Asymmetric baeyer-villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin. , 2002, Angewandte Chemie.

[273]  Rongcai Huang,et al.  Catalytic Asymmetric Cascade Vinylogous Mukaiyama 1,6-Michael/Michael Addition of 2-Silyloxyfurans with Azoalkenes: Direct Approach to Fused Butyrolactones. , 2015, Journal of the American Chemical Society.

[274]  Zheng Wang,et al.  Chiral Brønsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2. , 2008, Angewandte Chemie.

[275]  Yohan Park,et al.  Enantioselective Phase-Transfer Catalytic α-Benzylation and α-Allylation of α-tert-Butoxycarbonyllactones , 2013 .

[276]  S. V. Pansare,et al.  The organocatalytic vinylogous aldol reaction: recent advances. , 2011, Chemistry.

[277]  R. Bandichhor,et al.  Enantioselective synthesis of arglabin. , 2007, Angewandte Chemie.

[278]  Lili Lin,et al.  Enantioselective Baeyer-Villiger oxidation: desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones. , 2012, Journal of the American Chemical Society.

[279]  J. Genêt,et al.  C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions. , 2008, Angewandte Chemie.

[280]  Nobuhito Kurono,et al.  Enantiomer-selective carbamoylation of racemic alpha-hydroxy gamma-lactones with chiral Cu(II) Catalysts: an example of a highly active Lewis acid catalyzed reaction. , 2008, Chemistry, an Asian journal.

[281]  M. Doyle,et al.  A short stereoselective synthesis of (+)- and (−)-2-oxabicyclo[3.3.0]oct-6-en-3-one by intramolecular carbon–hydrogen insertion catalyzed by chiral dirhodium(II) carboxamidates , 2003 .

[282]  Giorgio Strukul,et al.  Transition Metal Catalysis in the Baeyer-Villiger Oxidation of Ketones. , 1998, Angewandte Chemie.

[283]  Zheng Wang,et al.  Mechanistic investigation of chiral phosphoric acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones with H2O2 as the oxidant. , 2010, Chemistry.

[284]  Mathieu Pucheault,et al.  Potassium trifluoro(organo)borates in rhodium-catalyzed 1,4-additions to α,β-unsaturated esters , 2005 .

[285]  R. Kitson,et al.  The renaissance of alpha-methylene-gamma-butyrolactones: new synthetic approaches. , 2009, Angewandte Chemie.

[286]  A. Paju,et al.  Asymmetric oxidation of cyclobutanones: modification of the Sharpless catalyst , 1998 .

[287]  B. Feringa,et al.  Highly enantioselective synthesis of 3-substituted γ-butenolides by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates. , 2012, Angewandte Chemie.

[288]  C. Curti,et al.  Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol , 2010 .

[289]  P. Langer New Strategies for the Development of an Asymmetric Version of the Baylis—Hillman Reaction , 2000 .

[290]  T. Wirth,et al.  Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications. , 2004, Chemical Society reviews.

[291]  J. Hartwig,et al.  Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran. , 2012, Journal of the American Chemical Society.

[292]  O. Reiser,et al.  Enantioselective synthesis of xanthatin. , 2014, Chemistry.

[293]  Tamio Hayashi,et al.  Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions. , 2003, Chemical reviews.

[294]  T. Mukaiyama,et al.  Effective synthesis of 5-substituted butenolide derivatives by using cinchonidine-derived quaternary ammonium phenoxide catalyst , 2007 .

[295]  S. Buchwald,et al.  Dynamic Kinetic Resolution of α,β‐Unsaturated Lactones through Asymmetric Copper‐Catalyzed Conjugate Reduction: Application to the Total Synthesis of Eupomatilone‐3 , 2005 .

[296]  Yoshihiko Yamamoto Transition-metal-catalyzed cycloisomerizations of α,ω-dienes. , 2012, Chemical reviews.

[297]  S. Hajra,et al.  Organocatalytic and enantioselective synthesis of beta-(hydroxyalkyl)-gamma-butyrolactones. , 2008, Journal of Organic Chemistry.

[298]  F. Toste,et al.  Catalytic enantioselective carbon-carbon bond formation using cycloisomerization reactions , 2012 .

[299]  C. Bolm,et al.  Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer–Villiger oxidation and epoxidation with chiral ligands , 2001 .

[300]  Vishnumaya Bisai Organocatalytic Asymmetric Vinylogous Aldol Reactions , 2012 .

[301]  N. Shimada,et al.  Asymmetric direct vinylogous aldol reaction of furanone derivatives catalyzed by an axially chiral guanidine base. , 2010, Angewandte Chemie.

[302]  B. Trost,et al.  Asymmetric Transition Metal-Catalyzed Allylic Alkylations. , 1996, Chemical reviews.

[303]  M. Doyle,et al.  Enantioselective carbon-hydrogen insertion is an effective and efficient methodology for the synthesis of (R)-(-)-baclofen. , 2002, Chirality.

[304]  Aurélie Claraz,et al.  Chiral Quaternary Ammonium Aryloxide/N,O‐Bis(trimethyl‐ silyl)acetamide Combination as Efficient Organocatalytic System for the Direct Vinylogous Aldol Reaction of (5H)‐Furan‐2‐one Derivatives , 2013 .

[305]  B. Feringa,et al.  Copper catalyzed asymmetric synthesis of chiral allylic esters. , 2006, Journal of the American Chemical Society.

[306]  E. Vedejs,et al.  Development of chiral nucleophilic pyridine catalysts: applications in asymmetric quaternary carbon synthesis. , 2003, Journal of the American Chemical Society.

[307]  K. Tomioka,et al.  4.7 C–C Bond Formation (Transition Metal-Catalyzed Michael) , 2012 .

[308]  E. Suresh,et al.  N-Heterocyclic Carbene Catalyzed Reaction of Enals and 1,2-Dicarbonyl Compounds: Stereoselective Synthesis of Spiro γ-Butyrolactones , 2006 .

[309]  Arun K. Ghosh,et al.  Enantioselective synthesis of (+)-cryptophycin 52 (LY355703), a potent antimitotic antitumor agent. , 2003, The Journal of organic chemistry.

[310]  C. Bolm,et al.  Catalyzed vinylogous Mukaiyama aldol reactions with controlled enantio- and diastereoselectivities. , 2009, Chemistry.

[311]  J. Vincent,et al.  A concise organocatalytic and enantioselective synthesis of isotetronic acids. , 2007, Chemical communications.

[312]  B. Trost,et al.  A "chiral aldehyde" equivalent as a building block towards biologically active targets. , 2004, Chemistry.

[313]  G. Desimoni,et al.  A new and highly efficient catalyst for the enantioselective Mukaiyama–Michael reaction between (E)-3-crotonoyl-1,3-oxazolidin-2-one and 2-trimethylsilyloxyfuran , 2001 .

[314]  Y. Yeung,et al.  Enantioselective bromolactonization using an S-alkyl thiocarbamate catalyst. , 2012, Angewandte Chemie.

[315]  B. Ashfeld,et al.  Enantioselective syntheses of tremulenediol A and tremulenolide A. , 2005, Organic letters.

[316]  K. Scheidt,et al.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis. , 2012, Angewandte Chemie.

[317]  J. Sweeney,et al.  Recent developments in the synthesis of furan-2(5H)-ones , 2002 .

[318]  N. Kumagai,et al.  A direct catalytic asymmetric aldol reaction of α-sulfanyl lactones: efficient synthesis of SPT inhibitors. , 2012, Angewandte Chemie.

[319]  D. Basavaiah,et al.  Recent advances in the Baylis-Hillman reaction and applications. , 2003, Chemical reviews.

[320]  K. Tsuchikama,et al.  Highly enantioselective construction of a chiral spirocyclic structure by the [2 + 2 + 2] cycloaddition of diynes and exo-methylene cyclic compounds. , 2006, Journal of the American Chemical Society.

[321]  S. Buchwald,et al.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes , 2015, Journal of the American Chemical Society.

[322]  B. Trost,et al.  Palladium-Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformation of 5-Acyloxy-2-(5H)-furanone. Enantioselective Synthesis of (−)-Aflatoxin B Lactone , 1999 .

[323]  E. Carreira,et al.  Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors. , 2004, Organic letters.

[324]  Tasuku Ito,et al.  Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acids , 1980 .

[325]  U. Hennecke New catalytic approaches towards the enantioselective halogenation of alkenes. , 2012, Chemistry, an Asian journal.

[326]  B. Trost,et al.  Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model. , 2006, Accounts of chemical research.

[327]  A. Mortreux,et al.  New one pot synthesis of a chiral α-hydroxy-γ-butyrolactone via sequential asymmetric hydrogenation of an α,γ-diketoester , 1998 .

[328]  L. Battistini,et al.  Advances in Exploring HeterocyclicDienoxysilane Nucleophiles in Asymmetric Synthesis , 2009 .

[329]  M. Snapper,et al.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism. , 2009, Journal of the American Chemical Society.

[330]  A. Gusso,et al.  Platinum-Catalyzed Oxidations with Hydrogen Peroxide: Enantiospecific Baeyer-Villiger Oxidation of Cyclic Ketones , 1994 .

[331]  Chao Fang,et al.  Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds. , 2012, Journal of the American Chemical Society.

[332]  T. Magauer,et al.  Total synthesis of the leucosceptroid family of natural products. , 2015, Journal of the American Chemical Society.

[333]  B. Trost,et al.  Asymmetric allylic alkylation, an enabling methodology. , 2004, The Journal of organic chemistry.

[334]  G. L. Hamilton,et al.  The progression of chiral anions from concepts to applications in asymmetric catalysis. , 2012, Nature chemistry.

[335]  Takao Saito,et al.  Recent Advances in Biaryl-Type Bisphosphine Ligands , 2005 .

[336]  K. Ishihara,et al.  Chiral hypervalent iodine-catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones , 2010 .

[337]  G. C. Fu,et al.  Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetals. , 2005, Journal of the American Chemical Society.

[338]  Chun‐Jiang Wang,et al.  Catalytic asymmetric construction of spiro(γ-butyrolactam-γ-butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides. , 2012, Chemistry.

[339]  O. Reiser,et al.  Enantioselective synthesis of (-)-paeonilide. , 2012, Chemical communications.

[340]  Claudio Cornaggia,et al.  Catalytic, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres. , 2012, Chemical communications.

[341]  S. Mukherjee,et al.  Catalytic asymmetric direct vinylogous Michael addition of deconjugated butenolides to maleimides for the construction of quaternary stereogenic centers. , 2012, Chemistry.

[342]  O. Reiser,et al.  Enantioselective synthesis of paraconic acids. , 2003, Chemistry.

[343]  D. Kim,et al.  Catalytic Enantioselective Bromolactonization of Alkenoic Acids in the Presence of Palladium Complexes. , 2013 .

[344]  M. Struchkova,et al.  A convenient route to chiral γ-lactones via asymmetric hydrogenation of γ-ketoesters using the RuCl3–BINAP–HCl catalytic system , 2008 .

[345]  R. D. Silva,et al.  Asymmetric synthesis of γ-butyrolactones by enantioselective hydrogenation of butenolides , 2003 .

[346]  Jieping Zhu,et al.  The Enantioselective Morita—Baylis—Hillman Reaction and Its Aza Counterpart , 2007 .

[347]  K. Nozaki,et al.  Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones , 1994 .

[348]  M. Shi,et al.  Multifunctional chiral phosphine organocatalysts in catalytic asymmetric Morita-Baylis-Hillman and related reactions. , 2010, Accounts of chemical research.

[349]  B. Siewert,et al.  Synthesis and Biological Evaluation of Antitumor‐Active Arglabin Derivatives , 2012, Archiv der Pharmazie.

[350]  S. Oudeyer,et al.  Recent advances in cooperative ion pairing in asymmetric organocatalysis. , 2012, Chemical Society reviews.

[351]  K. Ishihara,et al.  Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species. , 2010, Angewandte Chemie.

[352]  Davidr . Evans,et al.  C2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Scope and Mechanism of Catalytic Enantioselective Aldol Additions of Enolsilanes to (Benzyloxy)acetaldehyde , 1999 .

[353]  Vikas Kumar,et al.  Synergistic Lewis base and anion-binding catalysis for the enantioselective vinylogous addition of deconjugated butenolides to allenoates. , 2013, Chemical communications.

[354]  Z. Ge,et al.  Efficient direct asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones catalyzed by vicinal primary-diamine salts. , 2010, Chemical communications.

[355]  Dennis K. Taylor,et al.  1,2-Dioxines as Masked Cis γ-Hydroxy Enones and Their Versatility in the Synthesis of Highly Substituted γ-Lactones , 2002 .

[356]  Y. Zhang,et al.  Organocatalyzed Highly Enantioselective and anti-Selective Construction of γ-Butenolides through Vinylogous Mukaiyama Aldol Reaction , 2010 .

[357]  Feng Chen,et al.  Asymmetric bromolactonization using amino-thiocarbamate catalyst. , 2010, Journal of the American Chemical Society.

[358]  Xiyan Lu,et al.  Highly Enantioselective Palladium(II)-Catalyzed Cyclization of (Z)-4‘-Acetoxy-2‘-butenyl 2-Alkynoates: An Efficient Synthesis of Optically Active γ-Butyrolactones , 2000 .

[359]  S. Ma,et al.  Metal‐Catalyzed Enantioselective Allylation in Asymmetric Synthesis , 2008 .

[360]  P. Langer,et al.  New Strategies for the Development of an Asymmetric Version of the Baylis-Hillman Reaction This work was supported by the Fonds der Chemischen Industrie (Liebig-scholarship and funds for P. L.). P. L. thanks Prof. Dr. A. de Meijere for his support. , 2000, Angewandte Chemie.

[361]  W. Crowe,et al.  Gamma-butyrolactone synthesis via catalytic asymmetric cyclocarbonylation. , 2001, Journal of the American Chemical Society.