Absolute Asymmetric Synthesis of Tertiary a-Amino Acids

被引：21
|
作者：
Thi Thoa Mai [1 ]
Branca, Mathieu [1 ]
Gori, Didier [1 ]
Guillot, Regis [1 ]
Kouklovsky, Cyrille [1 ]
Alezra, Valerie [1 ]
机构：
[1] Univ Paris 11, Lab Chim Procedes & Subst Nat, CNRS, ICMMO,UMR 8182, F-91405 Orsay, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 20期
关键词：
amino acids; amides; asymmetric synthesis; chirality; synthetic methods; ENANTIOSELECTIVE SYNTHESIS; CHIRAL CRYSTALLIZATION; MOLECULAR CHIRALITY; OPTICAL-ACTIVITY; AROMATIC AMIDES; MEMORY; HOMOLOGATION; GENERATION; ROTATION; ACCESS;
D O I：
10.1002/anie.201200950
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsible for the stereoselectivity of the deprotonation/alkylation (see scheme). α-Amino acid derivatives are synthesized in up to 96% ee. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：4981 / 4984
页数：4
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