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

基金：

美国国家卫生研究院;

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

页码：1923 / 1926

页数：4

共 46 条

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