Direct organocatalytic asymmetric Mannich-type reactions in aqueous media:: one-pot Mannich-allylation reactions

被引：114
|
作者：
Córdova, A
Barbas, CF
机构：
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 09期
关键词：
D O I：
10.1016/S0040-4039(03)00019-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first direct organocatalytic asymmetric Mannich-type reactions in aqueous media are demonstrated herein. L-Proline-catalyzed reactions in aqueous media to provide beta-formyl substituted alpha-amino acid derivatives with excellent diastereoselectivities (dr up to 19:1, syn/anti) and high enantioselectivities (ee between 72 and >99%). These conditions provided for the development of novel one-pot asymmetric syntheses of cyclic gamma-allyl substituted alpha-amino acid derivatives (ee up to >99%). This was accomplished by combining the proline-catalyzed Mannich-type reactions with indium promoted allylations in aqueous media. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1923 / 1926
页数：4
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