Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

被引：256

作者：

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

PURE AND APPLIED CHEMISTRY | 2003年 / 75卷 / 01期

关键词：

D O I：

10.1351/pac200375010039

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including alpha-branched and alpha,alpha-dibranched amines, alpha- and beta-amino acids, 1,2- and 1,3-amino alcohols and alpha-trifluoromethyl amines are efficiently synthesized using this methodology.

引用

页码：39 / 46

页数：8

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