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
收藏
页码：11329 / 11332
页数：4
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