Asymmetric Mannich reactions catalyzed by cinchona alkaloid thiourea: enantioselective one-pot synthesis of novel β-amino ester derivatives

[1]  C. Barbas,et al.  Highly enantio- and diastereoselective Mannich reactions of glycine Schiff bases with in situ generated N-Boc-imines catalyzed by a cinchona alkaloid thiourea. , 2010, Organic Letters.

[2]  B. Feringa,et al.  Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: a new catalytic route to beta3-amino acids. , 2009, Journal of the American Chemical Society.

[3]  D. Kim,et al.  Organocatalytic highly enantio- and diastereoselective Mannich reaction of beta-ketoesters with N-Boc-aldimines. , 2009, The Journal of organic chemistry.

[4]  Lili Lin,et al.  Enantioselective three-component Kabachnik-Fields reaction catalyzed by chiral scandium(III)-N,N'-dioxide complexes. , 2009, Organic letters.

[5]  Jun Wang,et al.  Highly enantioselective aza-Henry reaction of ketoimines catalyzed by chiral N,N'-dioxide-copper(I) complexes. , 2008, Organic letters.

[6]  B. Tan,et al.  A highly diastereo- and enantioselective synthesis of multisubstituted cyclopentanes with four chiral carbons by the organocatalytic domino Michael-Henry reaction. , 2008, Organic letters.

[7]  James Gardiner,et al.  Beta-peptidic peptidomimetics. , 2008, Accounts of chemical research.

[8]  B. Alcaide,et al.  Organocatalytic reactions with acetaldehyde. , 2008, Angewandte Chemie.

[9]  Yongxin Li,et al.  Organocatalytic asymmetric tandem Michael-Henry reactions: a highly stereoselective synthesis of multifunctionalized cyclohexanes with two quaternary stereocenters. , 2008, Organic letters.

[10]  F. Tanaka,et al.  Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: importance of the 3-acid group on pyrrolidine for stereocontrol. , 2008, Journal of the American Chemical Society.

[11]  S. Schaus,et al.  Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic Applications , 2007 .

[12]  D. Ferraris.  Catalytic, Asymmetric Alkylation of Imines , 2007 .

[13]  M. Willis,et al.  Direct catalytic enantioselective mannich reactions : Synthesis of protected anti-α,β-diamino acids , 2007 .

[14]  Jun Song,et al.  Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst. , 2006, Journal of the American Chemical Society.

[15]  Jun Song,et al.  The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acids. , 2006, Journal of the American Chemical Society.

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

[17]  K. Scheidt,et al.  Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination. , 2006, Journal of the American Chemical Society.

[18]  Jinxing Ye,et al.  Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative. , 2006, Chemical communications.

[19]  J. V. van Maarseveen,et al.  Asymmetric organocatalytic Henry reaction. , 2006, Angewandte Chemie.

[20]  Baomin Wang,et al.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids. , 2006, Journal of the American Chemical Society.

[21]  Raquel P. Herrera,et al.  Enantioselective aza-Henry reaction using cinchona organocatalysts , 2006 .

[22]  S. Connon,et al.  Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance. , 2005, Angewandte Chemie.

[23]  Jinxing Ye,et al.  Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives. , 2005, Chemical communications.

[24]  S. Schaus,et al.  Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. , 2005, Journal of the American Chemical Society.

[25]  Jun Song,et al.  Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones. , 2005, Journal of the American Chemical Society.

[26]  A. Csámpai,et al.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. , 2005, Organic letters.

[27]  K. R. Knudsen,et al.  A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions. , 2005, Organic & biomolecular chemistry.

[28]  L. Deng,et al.  Highly Enantioselective Amination of α-Substituted α-Cyanoacetates with Chiral Catalysts Accessible from Both Quinine and Quinidine , 2005 .

[29]  E. Jacobsen,et al.  Highly enantioselective thiourea-catalyzed nitro-Mannich reactions. , 2005, Angewandte Chemie.

[30]  T. Lectka,et al.  Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of beta-lactams. , 2005, Journal of the American Chemical Society.

[31]  M. Terada,et al.  Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan. , 2004, Journal of the American Chemical Society.

[32]  L. Tang,et al.  Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. , 2004, Journal of the American Chemical Society.

[33]  L. Tang,et al.  Asymmetric organic catalysis with modified cinchona alkaloids. , 2004, Accounts of chemical research.

[34]  K. Jørgensen,et al.  Organocatalytic enantioselective conjugate addition to alkynones. , 2004, Journal of the American Chemical Society.

[35]  M. Snapper,et al.  Ag-catalyzed asymmetric mannich reactions of enol ethers with aryl, alkyl, alkenyl, and alkynyl imines. , 2004, Journal of the American Chemical Society.

[36]  Y. Takemoto,et al.  Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst. , 2004, Organic letters.

[37]  Y. Takemoto,et al.  Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. , 2003, Journal of the American Chemical Society.

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

[39]  L. Deng,et al.  Asymmetric alcoholysis of cyclic anhydrides. , 2003, Chemical reviews.

[40]  L. Deng,et al.  Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base. , 2003, Journal of the American Chemical Society.

[41]  E. Jacobsen,et al.  Privileged Chiral Catalysts , 2003, Science.

[42]  E. Jacobsen,et al.  Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids , 2002 .

[43]  Mei Fang Liu,et al.  Recent advances in the stereoselective synthesis of β-amino acids , 2002 .

[44]  Hongming Li,et al.  Development of a rapid, room-temperature dynamic kinetic resolution for efficient asymmetric synthesis of alpha-aryl amino acids. , 2002, Organic letters.

[45]  P. Váchal,et al.  Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction. , 2002, Journal of the American Chemical Society.

[46]  P. Perlmutter,et al.  β-amino acids: Versatile peptidomimetics , 2002 .

[47]  L. Tang,et al.  Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: asymmetric synthesis of alpha-hydroxy carboxylic acids. , 2002, Journal of the American Chemical Society.

[48]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

[49]  L. Deng,et al.  Asymmetric synthesis of alpha-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected alpha-amino acid N-carboxyanhydrides. , 2001, Journal of the American Chemical Society.

[50]  W. DeGrado,et al.  beta-Peptides: from structure to function. , 2001, Chemical reviews.

[51]  L. Deng,et al.  A highly enantioselective chiral Lewis base-catalyzed asymmetric cyanation of ketones. , 2001, Journal of the American Chemical Society.

[52]  T. Lectka,et al.  Catalytic, Asymmetric Synthesis of β-Lactams , 2000 .

[53]  M. Sigman,et al.  A General Catalyst for the Asymmetric Strecker Reaction This work was supported by the NIH (GM-43214). A postdoctoral fellowship to M.S.S. (NIH), and a predoctoral fellowship to P.V. sponsored by Alfred Bader are gratefully acknowledged. , 2000, Angewandte Chemie.

[54]  P. Váchal,et al.  Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quaternary amino acids. , 2000, Organic letters.

[55]  E. Juaristi,et al.  Recent advances in the enantioselective synthesis of beta-amino acids. , 1999, Current medicinal chemistry.

[56]  K. Gademann,et al.  β‐Peptides: Twisting and Turning , 1999 .

[57]  Eric N. Jacobsen,et al.  SCHIFF BASE CATALYSTS FOR THE ASYMMETRIC STRECKER REACTION IDENTIFIED AND OPTIMIZED FROM PARALLEL SYNTHETIC LIBRARIES , 1998 .

[58]  Samuel H. Gellman,et al.  Foldamers: A Manifesto , 1998 .

[59]  F. Rutjes,et al.  Organocatalysed asymmetric Mannich reactions. , 2008, Chemical Society reviews.

[60]  Y. Takemoto,et al.  Bifunctional-thiourea-catalyzed diastereo- and enantioselective aza-Henry reaction. , 2005, Chemistry.

[61]  D. Seebach,et al.  Preparation of Achiral and of Enantiopure Geminally Disubstituted β‐Amino Acids for β‐Peptide Synthesis , 2000 .

[62]  E. Juaristi.  Enantioselective synthesis of β-amino acids , 1997 .

[63]  C. Tomasini,et al.  Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids , 1996 .

[64]  D. Cole.  Recent stereoselective synthetic approaches to β-amino acids , 1994 .