Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Classical protocols for carbonyl allylation, propargylation and vinylation typically rely upon the use of preformed allyl metal, allenyl metal and vinyl metal reagents, respectively, mandating stoichiometric generation of metallic byproducts. Through transfer hydrogenative C-C coupling, however, carbonyl addition may be achieved from the aldehyde or alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. Here, we review transfer hydrogenative methods for carbonyl addition, which encompass the first catalytic protocols enabling direct C-H functionalization of alcohols.

[1]  J. Moreau Organometallic derivatives of allenes and ketenes , 2010 .

[2]  M. Krische,et al.  Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones. , 2008, Journal of the American Chemical Society.

[3]  Michael J. Krische,et al.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition. , 2008, Journal of the American Chemical Society.

[4]  M. Krische,et al.  Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level. , 2008, Chemistry letters.

[5]  M. Krische,et al.  Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: a ruthenium-catalyzed C-C bond-forming transfer hydrogenation. , 2008, Angewandte Chemie.

[6]  M. Krische,et al.  Ruthenium catalyzed C-C bond formation via transfer hydrogenation: branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes. , 2008, Organic letters.

[7]  M. Krische,et al.  Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogate. , 2008, Journal of the American Chemical Society.

[8]  M. Krische,et al.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents. , 2008, Journal of the American Chemical Society.

[9]  J. Hartwig,et al.  Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols. , 2008, Angewandte Chemie.

[10]  M. Krische,et al.  Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: design of effective monodentate TADDOL-like phosphonite ligands. , 2008, Journal of the American Chemical Society.

[11]  M. Krische,et al.  Iridium-catalyzed C-C coupling via transfer hydrogenation: carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene. , 2008, Organic Letters.

[12]  P. Guiry,et al.  Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde. , 2008, Organic & biomolecular chemistry.

[13]  J. A. Marshall,et al.  Synthesis and Reactions of Allenylmetal Compounds , 2008 .

[14]  P. Carroll,et al.  Catalytic asymmetric generation of (Z)-disubstituted allylic alcohols. , 2007, Journal of the American Chemical Society.

[15]  Nozomi Saito,et al.  Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands. , 2007, Organic letters.

[16]  M. Krische,et al.  Catalytic C-C coupling via transfer hydrogenation: reverse prenylation, crotylation, and allylation from the alcohol or aldehyde oxidation level. , 2007, Journal of the American Chemical Society.

[17]  P. Guiry,et al.  The Development of the Asymmetric Nozaki–Hiyama–Kishi Reaction , 2007 .

[18]  T. Jamison,et al.  Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes. , 2007, Chemical communications.

[19]  T. Ikariya,et al.  Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. , 2007, Accounts of chemical research.

[20]  M. Krische,et al.  Enantioselective iridium-catalyzed imine vinylation: optically enriched allylic amines via alkyne-imine reductive coupling mediated by hydrogen. , 2007, Journal of the American Chemical Society.

[21]  M. Krische,et al.  Carbonyl allylation in the absence of preformed allyl metal reagents: reverse prenylation via iridium-catalyzed hydrogenative coupling of dimethylallene. , 2007, Journal of the American Chemical Society.

[22]  M. Krische,et al.  Enantiomerically enriched allylic alcohols and allylic amines via C-C bond-forming hydrogenation: asymmetric carbonyl and imine vinylation. , 2007, Accounts of chemical research.

[23]  P. Guiry,et al.  New Proline–Oxazoline Ligands and Their Application in the Asymmetric Nozaki–Hiyama–Kishi Reaction , 2007 .

[24]  Young‐Taek Hong,et al.  Enantioselective Reductive Coupling of 1,3-Enynes to Glyoxalates Mediated by Hydrogen: Asymmetric Synthesis of β,γ-Unsaturated α-Hydroxy Esters , 2007 .

[25]  Jonathan M. J. Williams,et al.  Borrowing hydrogen in the activation of alcohols , 2007 .

[26]  D. Hall Lewis and Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds: From Discovery to Mechanism and Applications , 2007 .

[27]  J. A. Marshall Chiral allylic and allenic metal reagents for organic synthesis. , 2007, The Journal of organic chemistry.

[28]  M. Krische,et al.  Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen. , 2007, The Journal of organic chemistry.

[29]  M. Krische,et al.  Allylic amines via iridium-catalyzed C-C bond forming hydrogenation: imine vinylation in the absence of stoichiometric byproducts or metallic reagents. , 2007, Journal of the American Chemical Society.

[30]  M. Krische,et al.  Catalytic Reductive Coupling of Alkenes and Alkynes to Carbonyl Compounds and Imines Mediated by Hydrogen , 2007 .

[31]  M. Krische,et al.  Enantioselective reductive coupling of acetylene to N-arylsulfonyl imines via rhodium catalyzed C-C bond-forming hydrogenation: (Z)-dienyl allylic amines. , 2007, Journal of the American Chemical Society.

[32]  I. Marek,et al.  Creation of quaternary stereocenters in carbonyl allylation reactions. , 2007, Chemical communications.

[33]  Diego J. Ramón,et al.  C‐C‐Kupplungen mit Alkoholen als Elektrophilen: der Wasserstoff‐Autotransfer , 2007 .

[34]  M. Yus,et al.  Alcohols as electrophiles in C--C bond-forming reactions: the hydrogen autotransfer process. , 2007, Angewandte Chemie.

[35]  M. Krische,et al.  Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling. , 2007, The Journal of organic chemistry.

[36]  Shou‐Fei Zhu,et al.  Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: highly enantioselective synthesis of chiral bishomoallylic alcohols. , 2007, Journal of the American Chemical Society.

[37]  M. Kimura,et al.  Nickel-Catalyzed Reductive Coupling of Dienes and Carbonyl Compounds , 2007 .

[38]  M. Krische,et al.  Enantioselective reductive coupling of 1,3-enynes to heterocyclic aromatic aldehydes and ketones via rhodium-catalyzed asymmetric hydrogenation: mechanistic insight into the role of Brønsted acid additives. , 2006, Journal of the American Chemical Society.

[39]  M. Krische,et al.  Asymmetric induction in hydrogen-mediated reductive aldol additions to alpha-amino aldehydes catalyzed by rhodium: selective formation of syn-stereotriads directed by intramolecular hydrogen-bonding. , 2006, Journal of the American Chemical Society.

[40]  Young‐Taek Hong,et al.  Branch-selective intermolecular hydroacylation: hydrogen-mediated coupling of anhydrides to styrenes and activated olefins. , 2006, Angewandte Chemie.

[41]  S. Bräse,et al.  Second-Generation N,O-[2.2]Paracyclophane Ketimine Ligands for the Alkenylzinc Addition to Aliphatic and Aromatic Aldehydes: Scope and Limitations , 2006 .

[42]  T. Jamison,et al.  Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates. , 2006, Journal of the American Chemical Society.

[43]  P. Carroll,et al.  Direct, stereospecific generation of (Z)-disubstituted allylic alcohols. , 2006, Journal of the American Chemical Society.

[44]  M. Kimura,et al.  Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes. , 2006, Journal of the American Chemical Society.

[45]  T. Jamison,et al.  Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes. , 2006, Journal of the American Chemical Society.

[46]  P. Guiry,et al.  Application of Tridentate Bis(oxazoline) Ligands in Catalytic Asymmetric Nozaki–Hiyama Allylation and Crotylation: An Example of High Enantioselection with a Non‐Symmetric Bis(oxazoline) Ligand , 2006 .

[47]  Elisabetta Alberico,et al.  Asymmetric transfer hydrogenation: chiral ligands and applications. , 2006, Chemical Society reviews.

[48]  M. Krische,et al.  Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. , 2006, Organic letters.

[49]  M. Krische,et al.  Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation. , 2006, Journal of the American Chemical Society.

[50]  Chan-Mo Yu,et al.  Regulation of Stereoselectivity and Reactivity in the Inter- and Intramolecular Allylic Transfer Reactions , 2006 .

[51]  Kilian Muñiz Bifunktionale Metall‐Ligand‐Katalyse: Hydrierungen und neue Reaktionen an der Metall‐(Di)amin‐Einheit , 2005 .

[52]  Kilian Muñiz,et al.  Bifunctional metal-ligand catalysis: hydrogenations and new reactions within the metal-(di)amine scaffold. , 2005, Angewandte Chemie.

[53]  T. Jamison,et al.  Asymmetric Catalytic Reductive Coupling of 1,3‐Enynes and Aromatic Aldehydes , 2005 .

[54]  J. Montgomery,et al.  Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals. , 2005, Journal of the American Chemical Society.

[55]  M. Krische,et al.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation. , 2005, Journal of the American Chemical Society.

[56]  Y. Tu,et al.  A reaction for sp(3)-sp(3) C-C bond formation via cooperation of Lewis acid-promoted/Rh-catalyzed C-H bond activation. , 2005, Journal of the American Chemical Society.

[57]  T. Jamison,et al.  Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones. , 2005, Organic letters.

[58]  Justin P Roberts,et al.  Allylic etherification via Ir(I)/Zn(II) bimetallic catalysis. , 2005, Organic letters.

[59]  P. Walsh,et al.  Catalytic asymmetric vinylation and dienylation of ketones. , 2005, Journal of the American Chemical Society.

[60]  J. Soderquist,et al.  Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes. , 2005, Journal of the American Chemical Society.

[61]  Ryoji Noyori,et al.  Pursuing practical elegance in chemical synthesis. , 2005, Chemical communications.

[62]  P. Walsh,et al.  Catalytic asymmetric synthesis of hydroxy enol ethers: approach to a two-carbon homologation of aldehydes. , 2005, Organic letters.

[63]  Laurianne Bareille,et al.  First catalytic allyltitanation reactions. , 2005, Chemical communications.

[64]  P. Walsh,et al.  Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. , 2005, The Journal of organic chemistry.

[65]  Y. Masuyama,et al.  Rhodium-catalyzed carbonyl allylations by allylic alcohols with tin(II) chloride , 2004 .

[66]  J. L. Leighton,et al.  Highly diastereo- and enantioselective reagents for aldehyde crotylation. , 2004, Organic letters.

[67]  J. Hartwig,et al.  Iridium-catalyzed intermolecular allylic etherification with aliphatic alkoxides: asymmetric synthesis of dihydropyrans and dihydrofurans. , 2004, Angewandte Chemie.

[68]  C. Seto,et al.  Solid-phase synthesis of chiral N-acylethylenediamines and their use as ligands for the asymmetric addition of alkylzinc and alkenylzinc reagents to aldehydes. , 2004, The Journal of organic chemistry.

[69]  Young‐Taek Hong,et al.  Ru3(CO)12-catalyzed intramolecular allylic transfer reaction of tethered carbonyl group and allylic acetate moiety , 2004 .

[70]  J. Montgomery Nickel‐katalysierte reduktive Cyclisierungen und Kupplungen , 2004 .

[71]  J. Montgomery Nickel-catalyzed reductive cyclizations and couplings. , 2004, Angewandte Chemie.

[72]  P. Walsh,et al.  Catalytic asymmetric vinylation of ketones. , 2004, Journal of the American Chemical Society.

[73]  Hye‐Young Jang,et al.  Catalytic C-C bond formation via capture of hydrogenation intermediates. , 2004, Accounts of chemical research.

[74]  S. Sakaguchi,et al.  Allylation of alcohols and carboxylic acids with allyl acetate catalyzed by [Ir(cod)2](+)BF4- complex. , 2004, The Journal of organic chemistry.

[75]  Hye‐Young Jang,et al.  Hydrogen-mediated C-C bond formation: catalytic regio- and stereoselective reductive condensation of alpha-keto aldehydes and 1,3-enynes. , 2004, Journal of the American Chemical Society.

[76]  T. Jamison,et al.  Alkene-directed, nickel-catalyzed alkyne coupling reactions. , 2004, Journal of the American Chemical Society.

[77]  J. Montgomery,et al.  Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes. , 2004, Journal of the American Chemical Society.

[78]  I. Tredici,et al.  Enantioselective catalytic allylation of carbonyl groups by umpolung of pi-allyl palladium complexes. , 2004, Angewandte Chemie.

[79]  P. Wipf,et al.  Selective carbon–carbon bond formations with alkenylzirconocenes , 2004 .

[80]  D. Ha,et al.  Asymmetric Alkenylzinc Additions to Aldehydes Catalyzed by a Binaphthyl-Based N,O-Ligand , 2004 .

[81]  S. Dérien,et al.  Ruthenium-Catalyzed C–C Bond Formation , 2004 .

[82]  Shin‐ichi Ikeda Nickel‐katalysierte Kupplung von Carbonylverbindungen mit Alkinen oder 1,3‐Dienen zu Allyl‐, Homoallyl‐ und Bishomoallylalkoholen , 2003 .

[83]  S. Ikeda,et al.  Nickel-catalyzed coupling of carbonyl compounds and alkynes or 1,3-dienes: an efficient method for the preparation of allylic, homoallylic, and bishomoallylic alcohols. , 2003, Angewandte Chemie.

[84]  Dennis G. Hall,et al.  Aktivierung von Bor‐ und Siliciumreagentien bei stereokontrollierten Allylierungen , 2003 .

[85]  D. Hall,et al.  Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions. , 2003, Angewandte Chemie.

[86]  Hye‐Young Jang,et al.  A New catalytic C[bond]C bond-forming hydrogenation: reductive coupling of dienes and glyoxals under catalytic hydrogenation conditions. , 2003, Angewandte Chemie.

[87]  P. Walsh,et al.  A Catalytic Asymmetric Method for the Synthesis of γ-Unsaturated β-Amino Acid Derivatives , 2003 .

[88]  M. Kimura,et al.  Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources. , 2003, Angewandte Chemie.

[89]  S. Denmark,et al.  Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones. , 2003, Chemical reviews.

[90]  J. Hartwig,et al.  Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides. , 2003, Journal of the American Chemical Society.

[91]  T. Jamison,et al.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones. , 2003, Journal of the American Chemical Society.

[92]  K. Takai,et al.  Regioselective reductive coupling of alkynes and aldehydes leading to allylic alcohols. , 2003, Organic letters.

[93]  A. Chan,et al.  A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes. , 2003, The Journal of organic chemistry.

[94]  R. Noyori Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001). , 2003 .

[95]  T. Kondo,et al.  Advances in Ruthenium Catalysis. Novel Catalytic Reactions via η3- Allylruthenium Intermediates , 2002 .

[96]  P. Walsh,et al.  A general, highly enantioselective method for the synthesis of D and L alpha-amino acids and allylic amines. , 2002, Journal of the American Chemical Society.

[97]  T. Loh,et al.  Nickel-catalyzed homoallylation reaction of aldehydes with 1,3-dienes: stereochemical and mechanistic studies. , 2002, Organic letters.

[98]  R. Noyori Asymmetrische Katalyse: Kenntnisstand und Perspektiven (Nobel-Vortrag) Copyright© The Nobel Foundation 2002. – Wir danken der Nobel-Stiftung, Stockholm, für die Genehmigung zum Druck einer deutschen Fassung des Vortrags. , 2002 .

[99]  Pui Yee Ng,et al.  Strained silacycles in organic synthesis: a new reagent for the enantioselective allylation of aldehydes. , 2002, Journal of the American Chemical Society.

[100]  Ryoji Noyori,et al.  Asymmetric catalysis: science and opportunities (Nobel lecture). , 2002, Angewandte Chemie.

[101]  P. Wipf,et al.  Novel applications of alkenyl zirconocenes. , 2002, Chemistry.

[102]  Nozomi Saito,et al.  Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate. , 2002, The Journal of organic chemistry.

[103]  S. Bräse,et al.  [2,2]paracyclophane-based N,O-ligands in alkenylzinc additions to aldehydes. , 2001, Organic letters.

[104]  R. Noyori,et al.  Metal-ligand bifunctional catalysis: a nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds. , 2001, The Journal of organic chemistry.

[105]  M. Kimura,et al.  ChemInform Abstract: Nickel-Catalyzed Homoallylation of Aldehydes in the Presence of Water and Alcohols. , 2001 .

[106]  M. Kimura,et al.  Nickel-Catalyzed Homoallylation of Aldehydes in the Presence of Water and Alcohols We thank Mr. Y. Ohhama, NMR Facility, for his outstanding technical assistance. Financial support from the Ministry of Education, Science, Sports, and Culture, Japanese Government, Grant-in-Aid for Scientific Research , 2001, Angewandte Chemie.

[107]  S. Denmark,et al.  Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2'-bispyrrolidine-based bisphosphoramide. , 2001, Journal of the American Chemical Society.

[108]  W. Oppolzer,et al.  Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from omega-alkynals via intramolecular 1-alkenylzinc/aldehyde additions. , 2001, The Journal of organic chemistry.

[109]  B. Trost,et al.  Non-metathesis ruthenium-catalyzed C-C bond formation. , 2001, Chemical reviews.

[110]  S. Denmark,et al.  Lewis base activation of Lewis acids: catalytic enantioselective allylation and propargylation of aldehydes. , 2001, Journal of the American Chemical Society.

[111]  R. Noyori,et al.  Asymmetrische Katalyse mit hinsichtlich Struktur und Funktion gezielt entworfenen Molekülen: die chemo‐ und stereoselektive Hydrierung von Ketonen , 2001 .

[112]  Ryoji Noyori,et al.  Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones. , 2001, Angewandte Chemie.

[113]  Huang,et al.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes , 2000, Organic letters.

[114]  M. Kimura,et al.  Ni0-catalyzed regio- and stereoselective coupling reaction of Me3B, isoprene, and aldehydes , 2000 .

[115]  J. Montgomery,et al.  Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B , 2000 .

[116]  M. Bandini,et al.  The first catalytic enantioselective Nozaki–Hiyama–Kishi reaction , 2000 .

[117]  Marshall,et al.  Stereoselective synthesis of stereotriad subunits of polyketides through additions of nonracemic allenylsilanes to (R)- and (S)-2-methyl-3-oxygenated propanals , 2000, The Journal of organic chemistry.

[118]  J. S. Johnson,et al.  Chiral bis(oxazoline) copper(II) complexes: versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions. , 2000, Accounts of chemical research.

[119]  J. Montgomery,et al.  Nickel Catalysis in the Stereoselective Preparation of Quinolizidine, Pyrrolizidine, and Indolizidine Alkaloids: Total Synthesis of (+)-Allopumiliotoxin 267A , 1999 .

[120]  Y. Tamaru Novel catalytic reactions involving π-allylpalladium and -nickel as the key intermediates: umpolung and β-decarbopalladation of π-allylpalladium and nickel-catalyzed homoallylation of carbonyl compounds with 1,3-dienes , 1999 .

[121]  Masanari Kimura,et al.  Die Nickel‐katalysierte Homoallylierung von Aldehyden und Ketonen mit 1,3‐Dienen und ihre komplementäre Unterstützung durch Diethylzink und Triethylboran , 1999 .

[122]  M. Kimura,et al.  Nickel-Catalyzed Homoallylation of Aldehydes and Ketones with 1,3-Dienes and Complementary Promotion by Diethylzinc or Triethylborane. , 1999, Angewandte Chemie.

[123]  M. Kimura,et al.  Novel carbonyl-dependent regioselective allylation via diethylzinc-mediated umpolung of π-allylpalladium , 1998 .

[124]  P. Wipf,et al.  Zirconocene−Zinc Transmetalation and in Situ Catalytic Asymmetric Addition to Aldehydes , 1998 .

[125]  M. Mori,et al.  Nickel-catalyzed regio- and stereoselective synthesis of homoallylic alcohol derivatives from dienes and aldehydes , 1998 .

[126]  K. Wada,et al.  First Intermolecular Hydroacylation of 1,3-Dienes with Aldehydes Catalyzed by Ruthenium , 1998 .

[127]  M. Kimura,et al.  NOVEL AND HIGHLY REGIO- AND STEREOSELECTIVE NICKEL-CATALYZED HOMOALLYLATION OF BENZALDEHYDE WITH 1,3-DIENES , 1998 .

[128]  J. Montgomery,et al.  A New Stereoselective Method for the Preparation of Allylic Alcohols , 1997 .

[129]  and Ryoji Noyori,et al.  Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes , 1997 .

[130]  A. Fürstner,et al.  A MULTICOMPONENT REDOX SYSTEM ACCOUNTS FOR THE FIRST NOZAKI-HIYAMA-KISHI REACTIONS CATALYTIC IN CHROMIUM , 1996 .

[131]  J. A. Marshall Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric Synthesis. , 1996, Chemical reviews.

[132]  Carsten Bolm,et al.  Catalytic Asymmetric Carbonyl–Ene Reactions , 1995 .

[133]  C. Bolm,et al.  Katalytische asymmetrische Carbonyl‐En‐Reaktionen , 1995 .

[134]  W. Crowe,et al.  Titanium-Catalyzed Reductive Cyclization of .delta.,.epsilon.-Unsaturated Ketones and Aldehydes , 1995 .

[135]  S. Buchwald,et al.  Reductive Cyclization of Enones by a Titanium Catalyst , 1995 .

[136]  W. Oppolzer,et al.  Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal ester , 1995 .

[137]  H. Ono,et al.  NUCLEOPHILIC AND ELECTROPHILIC ALLYLATION REACTIONS. SYNTHESIS, STRUCTURE,AND AMBIPHILIC REACTIVITY OF (ETA 3-ALLYL)RUTHENIUM(II) COMPLEXES , 1995 .

[138]  Xiaoming Chen,et al.  Asymmetric synthesis of homopropargylic alcohols from aldehydes and allenyltri-n-butylstannane , 1994 .

[139]  S. Denmark,et al.  Asymmetric Allylation of Aldehydes with Chiral Lewis Bases , 1994 .

[140]  P. Wipf,et al.  Preparation of allylic alcohols by alkene transfer from zirconium to zinc , 1994 .

[141]  I. Ojima,et al.  Extremely Chemoselective Silylformylation and Silylcarbocyclization of Alkynals , 1994 .

[142]  K. Soai,et al.  Asymmetric alkenylation of chiral and prochiral aldehydes catalysed by chiral or achiral amino alcohols: catalytic diastereoselective synthesis of protected erythro-sphingosine and enantioselective synthesis of chiral diallyl alcohols , 1994 .

[143]  G. E. Keck,et al.  Catalytic asymmetric allylation of aldehydes , 1993 .

[144]  A. Costa,et al.  Catalytic asymmetric synthesis of homoallylic alcohols , 1993 .

[145]  W. Oppolzer,et al.  Synthesis of (R)-(-)-muscone by an asymmetrically catalyzed macrocyclization of an .omega.-alkynal , 1993 .

[146]  Y. Uozumi,et al.  Axially chiral allenylboranes: catalytic asymmetric synthesis by palladium-catalysed hydroboration of but-1-en-3-ynes and their reaction with an aldehyde , 1993 .

[147]  K. Mikami,et al.  ASYMMETRIC ENE REACTIONS IN ORGANIC SYNTHESIS , 1992 .

[148]  S. Gladiali,et al.  Asymmetric Hydrogen Transfer Reactions Promoted by Homogeneous Transition Metal Catalysts , 1992 .

[149]  Y. Masuyama,et al.  Palladium-catalyzed carbonyl allylation by allylic alcohols with stannous chloride , 1992 .

[150]  W. Oppolzer,et al.  Catalytic asymmetric synthesis of Secondary (E)-allyl alcohols from acetylenes and aldehydes via (1-alkenyl)zinc intermediates. Preliminary Communication , 1992 .

[151]  P. Kalck,et al.  Hydroformylation Catalyzed by Ruthenium Complexes , 1993 .

[152]  Michael G. Yang,et al.  Diastereofacial selectivity with optically active .alpha.-substituted .beta.-silyl-(E)-hexenoates. Enantioselective construction of homoallylic ethers via reaction with aryl acetals , 1991 .

[153]  J. A. Marshall,et al.  Highly diastereoselective SE' additions of enantioenriched allenylstannanes to (S)-2-(benzyloxy)propanal , 1991 .

[154]  K. Furuta,et al.  Chiral (Acyloxy)borane Catalyzed Asymmetric Allylation of Aldehydes , 1992 .

[155]  T. Mukai,et al.  Ruthenium-catalyzed allylation of primary alcohols by allylic acetates: a novel synthesis of .alpha.,.beta.-unsaturated ketones , 1991 .

[156]  E. Corey,et al.  A practical and general enantioselective synthesis of chiral propa-1,2-dienyl and propargyl carbinols , 1990 .

[157]  T. Mukai,et al.  Ruthenium complex catalyzed allylation of aldehydes with allylic acetates , 1989 .

[158]  E. Corey,et al.  A practical and efficient method for enantioselective allylation of aldehydes , 1989 .

[159]  R. O. Duthaler,et al.  Enantioselektive Allylierung von Carbonylverbindungen mit Titan‐Kohlenhydrat‐Komplexen , 1989 .

[160]  R. Duthaler,et al.  Enantioselective Allylation of Carbonyl Compounds with Titanium‐Carbohydrate Complexes , 1989 .

[161]  S. Masamune,et al.  Asymmetric allylboration with B-allyl-2-(trimethylsilyl)borolane , 1989 .

[162]  M. Reetz Asymmetric C-C bond formation using organometallic chemistry , 1988 .

[163]  T. Mukaiyama,et al.  Asymmetric Allylation with a New Chiral Allylating Agent Prepared from Tin(II) Triflate, Chiral Diamine, and Allylaluminum , 1987 .

[164]  D. Seebach,et al.  Chirale Alkoxytitan(IV)‐Komplexe für enantioselektive nucleophile Additionen an Aldehyde und als Lewis‐Säuren in Diels‐Alder‐Reaktionen , 1987 .

[165]  R. Noyori,et al.  Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes. , 1986, Journal of the American Chemical Society.

[166]  J. Inanaga,et al.  Reductive coupling of allylic acetates with carbonyl compounds by using Pd(0)-SmI2 system , 1986 .

[167]  W. Roush,et al.  Diastereo- and enantioselective aldehyde addition reactions of 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic esters, a useful class of tartrate ester modified allylboronates , 1985 .

[168]  N. Oguni,et al.  Enantioselective addition of diethylzinc to benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols , 1984 .

[169]  P. Jadhav,et al.  Asymmetric carbon-carbon bond formation via .beta.-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric purities , 1983 .

[170]  Hisashi Yamamoto,et al.  Chiral allenylboronic esters: a practical reagent for enantioselective carbon-carbon bond formation , 1982 .

[171]  M. Kumada,et al.  Optically active allylsilanes. 2. High stereoselectivity in asymmetric reaction with aldehydes producing homoallylic alcohols , 1982 .

[172]  H. Sakurai Reactions of allylsilanes and application to organic synthesis , 1982 .

[173]  MukaiyamaTeruaki,et al.  A CONVENIENT SYNTHESIS OF α-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE , 1981 .

[174]  R. Hoffmann,et al.  Stereoselektive Synthese von Alkoholen, VII1) Optisch aktive Homoallylalkohole durch Addition chiraler Boronsäureester an Aldehyde , 1981 .

[175]  D. Carini,et al.  (Trimethylsilyl)allenes as propargylic anion equivalents: synthesis of homopropargylic alcohols and ethers , 1980 .

[176]  R. W. Hoffmann,et al.  Enantioselective Synthesis of Homoallyl Alcohols via Chiral Allylboronic Esters , 1978 .

[177]  R. Hoffmann,et al.  Enantioselektive Synthese von Homoallylalkoholen über chirale Allylboronsäure‐ester , 1978 .

[178]  A. Hosomi,et al.  Syntheses of γ,δ-unsaturated alcohols from allylsilanes and carbonyl compounds in the presence of titanium tetrachloride☆ , 1976 .

[179]  A. Dobson,et al.  Complexes of the platinum metals. Part V. Perfluorocarboxylato-derivatives , 1975 .

[180]  M. Lequan,et al.  Réaction de condensation des dérivés propargyliques et alléniques de l'étain sur le chloralétude cinétique , 1973 .

[181]  J. H. Wotiz The Propargylic Rearrangement. I. The Carbonation Products of Grignard Reagents from Primary Propargylic Bromides , 1950 .