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

页码：4981 / 4984

页数：4

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