AN ASYMMETRIC AMMONIA SYNTHON FOR MICHAEL ADDITIONS

被引：68

作者：

HAWKINS, JM

LEWIS, TA

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 07期

关键词：

D O I：

10.1021/jo00033a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.

引用

页码：2114 / 2121

页数：8

共 42 条

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