Chiral proton catalysis: Enantioselective bronsted acid catalyzed additions of nitroacetic acid derivatives as glycine equivalents

被引：139

作者：

Singh, Anand ^{[1
]}

Yoder, Ryan A. ^{[1
]}

Shen, Bo ^{[1
]}

Johnston, Jeffrey N. ^{[1
]}

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 12期

关键词：

D O I：

10.1021/ja068073r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unsymmetrical, bifunctional chiral proton catalyst ( 2) has been developed to enable the highly diastereo- and enantioselective synthesis of epimerizable addition products from nitroacetic acid esters. The strategy is analogous to O'Donnell's glycine Schiff base alkylations that have been broadly applied to the synthesis of alpha-amino acids. In this regard, nitroacetic acid esters provide complementary products, namely, anti-alpha,beta-diamino acids, derived from addition reactions. Products are obtained with high diastereoselection (generally 6-12:1) and enantioselection (generally > 90% ee) using 5 mol% catalyst loading.

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页码：3466 / +

页数：3

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