Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system

被引：138

作者：

Lili Cheng

Xiaoyu Wu

Yixin Lu

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[2] Natl Univ Singapore, Med Chem Program, Off Life Sci, Singapore 117543, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 07期

关键词：

D O I：

10.1039/b701579h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct three-component Mannich reactions of O-benzyl hydroxyacetone with p-anisidine and aromatic or aliphatic aldehydes in the presence of an L-threonine-derived catalyst afforded anti-1,2-amino alcohols in good-to-excellent yields and with enantioselectivities of up to 97%. This study is the first demonstration that direct three-component Mannich reactions can be promoted by a primary amino acid in water.

引用

页码：1018 / 1020

页数：3

共 40 条

[1] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[2] 2-E
[3] Berkssel A., 2005, ASYMMETRIC ORGANOCAT
[4] Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives
Bernardi, L
Gothelf, AS
Hazell, RG
Jorgensen, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) : 2583 - 2591
[5] Enamine-based aldol organocatalysis in water: Are they really "all wet"?
Brogan, Andrew P.
Dickerson, Tobin J.
Janda, Kim D.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) : 8100 - 8102
[6] The direct catalytic asymmetric Mannich reaction
Córdova, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112
[7] One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives
Córdova, A
[J]. SYNLETT, 2003, (11) : 1651 - 1654
[8] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids
Córdova, A
Notz, W
Zhong, GF
Betancort, JM
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1842 - 1843
[9] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[10] Denmark S. E., 1999, COMPREHENSIVE ASYMME, P923

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