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

被引：331
|
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.
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页码：8883 / 8904
页数：22
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