Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins

被引:156
作者
Xu, YM [1 ]
Córdova, A [1 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden
关键词
D O I
10.1039/b514783m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple, highly modular primary amino acid derivatives catalyze the direct enantioselective addition of ketones to nitro-olefins with high stereocontrol and furnish the corresponding aldol products in high yield with up to > 38 : 1 dr and up to 99% ee.
引用
收藏
页码:460 / 462
页数:3
相关论文
共 49 条
[1]   Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].
Alexakis, A ;
Andrey, O .
ORGANIC LETTERS, 2002, 4 (21) :3611-3614
[2]   The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].
Andrey, O ;
Alexakis, A ;
Tomassini, A ;
Bernardinelli, G .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168
[3]   Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].
Andrey, O ;
Alexakis, A ;
Bernardinelli, G .
ORGANIC LETTERS, 2003, 5 (14) :2559-2561
[4]   The discovery of catalytically active peptides through combinatorial chemistry [J].
Berkessel, A .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (03) :409-419
[5]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[6]   Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Tanaka, F ;
Barbas, CF .
SYNTHESIS-STUTTGART, 2004, (09) :1509-1521
[7]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[8]   Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Barbas, CF .
TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444
[9]   Direct amino acid catalyzed asymmetric synthesis of polyketide sugars [J].
Casas, J ;
Engqvist, M ;
Ibrahem, I ;
Kaynak, B ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1343-1345
[10]   Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].
Christoffers, J ;
Baro, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690