Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines

被引：336

作者：

Cogan, DA ^{[1
]}

Liu, GC ^{[1
]}

Ellman, J ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 29期

关键词：

amines; asymmetric reactions; diastereoselection; imines; sulfinamides;

D O I：

10.1016/S0040-4020(99)00451-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High yielding and highly diastereoselective methods for I,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert-butanesulfinyl ketimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched alpha-branched and alpha,alpha-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8883 / 8904

页数：22