Dipeptide-catalyzed direct asymmetric aldol reaction

被引：82

作者：

Shi, LX ^{[1
]}

Sun, Q ^{[1
]}

Ge, ZM ^{[1
]}

Zhu, YQ ^{[1
]}

Cheng, TM ^{[1
]}

Li, RT ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China

来源：

SYNLETT | 2004年 / 12期

关键词：

aldol reaction; organocatalysis; enamine catalysis; dipeptides;

D O I：

10.1055/s-2004-831324

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(L)-H-Pro-(L)-Phe-OH (4) were found to be efficient catalysts for direct asymmetric aldol reactions between acetone and various aldehydes. The reaction conditions use a DMSO-NMM-PEMG 5000 system at 0 degreesC in high yields (62-96%) and enantioselectivities (up to >99% ee).

引用

页码：2215 / 2217

页数：3

共 24 条

[1] The direct catalytic asymmetric cross-aldol reaction of aldehydes
Alcaide, B
Almendros, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) : 858 - 860
[2] Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
[3] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
Bahmanyar, S
Houk, KN
Martin, HJ
List, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) : 2475 - 2479
[4] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
Córdova, A
Notz, W
Barbas, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303
[5] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[6] 2-D
[7] Aqueous aldol catalysis by a nicotine metabolite
Dickerson, TJ
Janda, KD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) : 3220 - 3221
[8] Gröger H, 2001, ANGEW CHEM INT EDIT, V40, P529
[9] Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions
Hoang, L
Bahmanyar, S
Houk, KN
List, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 16 - 17
[10] Amino acids and peptides as asymmetric organocatalysts
Jarvo, ER
Miller, SJ
[J]. TETRAHEDRON, 2002, 58 (13) : 2481 - 2495

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