Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes

被引：37

作者：

Phelan, James P. ^{[1
]}

Patel, Evan J. ^{[1
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 42期

关键词：

asymmetric catalysis; michael addition; nitroalkene; organocatalysis; MICHAEL ADDITION; THIOACETIC ACID; DRUG DISCOVERY; DERIVATIVES; OXETANES; MALONATE; ANALOGS;

D O I：

10.1002/anie.201406971

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes to produce highly enantioenriched products with a tetrasubstituted carbon is reported. Thioacids added in excellent yields and with high enantioselectivities to both activated and unactivated nitroalkenes. The 1,2-nitrothioacetate products can be readily converted in two steps to biomedically relevant 1,2-aminosulfonic acids without loss of enantiopurity.

引用

页码：11329 / 11332

页数：4

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