Small peptide-catalyzed enantioselective addition of ketones to nitroolefins

被引：132

作者：

Xu, YM ^{[1
]}

Zou, WB ^{[1
]}

Sundén, H ^{[1
]}

Ibrahem, S ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 4-5期

关键词：

asymmetric catalysis; ketones; Michael reaction; nitroolefins; peptides;

D O I：

10.1002/adsc.200505373

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The direct small peptide-catalyzed enantioselective Michael addition of ketones to nitroolefins is presented. Simple di- and tripeptides derived from alanine catalyze the asymmetric Michael additions with high stereoselectivity and furnish the corresponding Michael products in high yield with up to 68: 1 dr and 98% ee. The study demonstrates that small, readily prepared peptides with increased structural complexity as compared to the parent amino acid mediate the asymmetric Michael reaction with superior reactivity and enantioselectivity.

引用

页码：418 / 424

页数：7

共 56 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. 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
Andrey, O
Alexakis, A
Tomassini, A
Bernardinelli, G
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
[3] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
Andrey, O
Alexakis, A
Bernardinelli, G
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
[4] The discovery of catalytically active peptides through combinatorial chemistry
Berkessel, A
[J]. 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
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
[J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
[7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
Betancort, JM
Barbas, CF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
[8] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
Betancort, JM
Sakthivel, K
Thayumanavan, R
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
[9] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
Christoffers, J
Baro, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
[10] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
Cobb, AJA
Shaw, DM
Longbottom, DA
Gold, JB
Ley, SV
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96

← 1 2 3 4 5 6 →