Phosphine-catalyzed asymmetric [3 + 2] annulation of chalcones with allenoates for enantioselective synthesis of functionalized cyclopentenes

Chiral phosphine-catalyzed asymmetric [3 + 2] annulation reaction of various Boc-amino-substituted chalcones with allenoates has been developed, leading to efficient formation of 1,4,5-trisubstituted cyclopentenes with high yields, excellent diastereoselectivities and enantioselectivities (up to 99% ee and up to 98% yield).

[1]  Y. Huang,et al.  Morita-Baylis-Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation. , 2015, Organic & biomolecular chemistry.

[2]  Pascal Retailleau,et al.  Phosphahelicenes in asymmetric organocatalysis: [3+2] cyclizations of γ-substituted allenes and electron-poor olefins. , 2015, Angewandte Chemie.

[3]  Y. Fujiwara,et al.  Phosphine-Catalyzed Enantioselective Intramolecular [3+2] Annulations To Generate Fused Ring Systems , 2015, Journal of the American Chemical Society.

[4]  O. Kwon,et al.  Chiral phosphines in nucleophilic organocatalysis , 2014, Beilstein journal of organic chemistry.

[5]  O. Kwon,et al.  Phosphine catalysis of allenes with electrophiles. , 2014, Chemical Society reviews.

[6]  O. Kwon,et al.  Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs. , 2013, Chemical communications.

[7]  Jun‐An Ma,et al.  Bisphosphine-triggered one-pot sequential [3 + 2]/[3 + 2] annulation of allenoates with cyclic ketimines. , 2013, Organic letters.

[8]  N. Martín,et al.  Asymmetric organocatalysis in fullerenes chemistry: enantioselective phosphine-catalyzed cycloaddition of allenoates onto C60. , 2013, Angewandte Chemie.

[9]  M. Shi,et al.  Phosphine-Catalyzed [3 + 2] Cycloaddition of 4,4-Dicyano-2-methylenebut-3-enoates with Benzyl Buta-2,3-dienoate and Penta-3,4-dien-2-one , 2013 .

[10]  Zhengjie He,et al.  Phosphine-catalyzed [3+2] annulation of α-substituted allenoates with ester-activated α,β-unsaturated imines: a novel variation of the Lu [3+2] cycloaddition reaction. , 2013, Chemical communications.

[11]  Yixin Lu,et al.  Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines. , 2012, Organic letters.

[12]  Yixin Lu,et al.  Highly enantioselective [4 + 2] annulations catalyzed by amino acid-based phosphines: Synthesis of functionalized cyclohexenes and 3-spirocyclohexene-2-oxindoles , 2012 .

[13]  M. Shi,et al.  Construction of adjacent spiro-quaternary and tertiary stereocenters through phosphine-catalyzed asymmetric [3+2] annulation of allenoates with alkylidene azlactones. , 2012, Chemical communications.

[14]  P. Retailleau,et al.  Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine‐Catalyzed [3+2] Annulations , 2012 .

[15]  Yixin Lu,et al.  Versatile enantioselective [3+2] cyclization between imines and allenoates catalyzed by dipeptide-based phosphines. , 2012, Angewandte Chemie.

[16]  M. Shi,et al.  Development of asymmetric phosphine-promoted annulations of allenes with electron-deficient olefins and imines. , 2012, Chemical communications.

[17]  M. Shi,et al.  Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers. , 2012, Chemical communications.

[18]  K. Jørgensen,et al.  Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction , 2011, Chemistry.

[19]  Y. Fujiwara,et al.  Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters. , 2011, Journal of the American Chemical Society.

[20]  A. Marinetti,et al.  Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones , 2011 .

[21]  Shou‐Fei Zhu,et al.  Chiral Spiro Ligands , 2011 .

[22]  M. Shi,et al.  Phosphine- and nitrogen-containing Lewis base catalyzed highly regioselective and geometric selective cyclization of isatin derived electron-deficient alkenes with ethyl 2,3-butadienoate. , 2011, Organic letters.

[23]  P. Retailleau,et al.  Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations. , 2011, Chemical communications.

[24]  Yixin Lu,et al.  Enantioselective [3 + 2] cycloaddition of allenes to acrylates catalyzed by dipeptide-derived phosphines: facile creation of functionalized cyclopentenes containing quaternary stereogenic centers. , 2011, Journal of the American Chemical Society.

[25]  T. Loh,et al.  Highly enantio-, regio- and diastereo-selective one-pot [2 + 3]-cycloaddition reaction via isomerization of 3-butynoates to allenoates , , 2010 .

[26]  P. Retailleau,et al.  An organocatalytic [3+2] cyclisation strategy for the highly enantioselective synthesis of spirooxindoles. , 2010, Chemistry.

[27]  A. Marinetti,et al.  Studies on the asymmetric, phosphine-promoted [3+2] annulations of allenic esters with 2-aryl-1,1-dicyanoalkenes , 2010 .

[28]  Gang Zhao,et al.  Asymmetric [3+2] cycloadditions of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines. , 2010, Angewandte Chemie.

[29]  A. Marinetti,et al.  Enantioselective Phosphine Organocatalysis , 2010 .

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

[31]  P. Retailleau,et al.  Expanding the scope of enantioselective ferroPHANE-promoted [3+2] annulations with alpha,beta-unsaturated ketones. , 2010, Chemistry.

[32]  G. C. Fu,et al.  Stereoselective phosphine-catalyzed synthesis of highly functionalized diquinanes. , 2010, Angewandte Chemie.

[33]  Scott J. Miller,et al.  Enantioselective catalysis and complexity generation from allenoates. , 2009, Chemical Society reviews.

[34]  P. Retailleau,et al.  Synthesis of Chiral 2‐Phospha[3]ferrocenophanes and their Behaviour as Organocatalysts in [3+2] Cyclization Reactions , 2009 .

[35]  Scott J. Miller,et al.  The Rauhut–Currier reaction: a history and its synthetic application , 2009 .

[36]  Wei Zhang,et al.  Highly enantioselective copper-catalyzed ring opening of oxabicyclic alkenes with Grignard reagents. , 2008, Chemistry, an Asian journal.

[37]  P. Retailleau,et al.  2-Phospha[3]ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations. , 2008, Journal of the American Chemical Society.

[38]  Jian Zhou,et al.  Phosphine-triggered synthesis of functionalized cyclic compounds. , 2008, Chemical Society reviews.

[39]  E. Jacobsen,et al.  Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions. , 2008, Journal of the American Chemical Society.

[40]  Qi‐Lin Zhou,et al.  Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions. , 2008, Accounts of chemical research.

[41]  Satoshi Omura,et al.  Efficient total synthesis of novel bioactive microbial metabolites. , 2008, Accounts of chemical research.

[42]  E. Plettner,et al.  Screening of dialkoxybenzenes and disubstituted cyclopentene derivatives against the cabbage looper, Trichoplusia ni, for the discovery of new feeding and oviposition deterrents. , 2007, Journal of agricultural and food chemistry.

[43]  Scott J. Miller,et al.  Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing alpha-amino acid. , 2007, Journal of the American Chemical Society.

[44]  O. Kwon,et al.  Phosphine-catalyzed synthesis of highly functionalized coumarins. , 2007, Organic letters.

[45]  O. Kwon,et al.  Phosphine triggered [3+2] allenoate–acrylate annulation: a mechanistic enlightenment , 2007 .

[46]  Lei Jiao,et al.  An unexpected role of a trace amount of water in catalyzing proton transfer in phosphine-catalyzed (3 + 2) cycloaddition of allenoates and alkenes. , 2007, Journal of the American Chemical Society.

[47]  R. Reamer,et al.  Phosphine-catalyzed cycloadditions of allenic ketones: new substrates for nucleophilic catalysis. , 2007, The Journal of organic chemistry.

[48]  R. Menon,et al.  Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: A promising synthetic strategy. , 2006, Accounts of chemical research.

[49]  Shou‐Fei Zhu,et al.  Preparation and application of bisoxazoline ligands with a chiral spirobiindane skeleton for asymmetric cyclopropanation and allylic oxidation , 2006 .

[50]  G. C. Fu,et al.  Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enones. , 2006, Angewandte Chemie.

[51]  B. Skelton,et al.  Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3 + 2]-cycloadditions to 5-methylenehydantoins. , 2005, The Journal of organic chemistry.

[52]  O. Kwon,et al.  A Highly Diastereoselective Synthesis of 3‐Carbethoxy‐2,5‐disubstituted‐3‐pyrrolines by Phosphine Catalysis. , 2005 .

[53]  B. Liu,et al.  Synthesis and application of chiral spiro phospholane ligand in Pd-catalyzed asymmetric allylation of aldehydes with allylic alcohols. , 2005, Organic letters.

[54]  W. Roush,et al.  Nucleophilic Phosphine Organocatalysis , 2004 .

[55]  M. Krische,et al.  Catalytic diastereoselective synthesis of diquinanes from acyclic precursors. , 2003, Journal of the American Chemical Society.

[56]  X. Lu,et al.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis. , 2001, Accounts of chemical research.

[57]  Xiyan Lu,et al.  Phosphine-catalyzed[3+2] cycloaddition reaction of methyl 2, 3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles , 1997 .

[58]  G. Zhu,et al.  Asymmetric [3 + 2] Cycloaddition of 2,3-Butadienoates with Electron-Deficient Olefins Catalyzed by Novel Chiral 2,5-Dialkyl-7-phenyl-7- phosphabicyclo[2.2.1]heptanes , 1997 .

[59]  K. Schafer,et al.  Synthesis of novel conformationally restricted L-glutamate analogues , 1997 .

[60]  Xiyan Lu,et al.  Phosphine-Catalyzed Cycloaddition of 2,3-Butadienoates or 2-Butynoates with Electron-Deficient Olefins. A Novel [3 + 2] Annulation Approach to Cyclopentenes , 1995 .