STEREOSELECTIVE REACTIONS .23. ASYMMETRIC MICHAEL REACTION OF ALPHA-ALKYL BETA-KETO-ESTERS VIA CHIRAL ENAMINES - DEPENDENCE OF THE DIASTEREOFACIAL SELECTION ON THE COMBINATION OF SOLVENTS AND ADDITIVES

被引：21

作者：

ANDO, K ^{[1
]}

YASUDA, K ^{[1
]}

TOMIOKA, K ^{[1
]}

KOGA, K ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 03期

关键词：

D O I：

10.1039/p19940000277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Michael reaction of the chiral enamines prepared from alpha-alkyl beta-keto esters and (S)-valine tert-butyl ester is described. The diastereoselectivity of this reaction is highly sensitive to the solvent system; The lithiated chiral enamines react with di-tert-butyl methylenemalonate in toluene-HMPA to give alpha,alpha-dialkylated beta-keto esters in 87-92% ee after hydrolysis. On the other hand. the reactions in THF give the corresponding antipodes in 84-95% ee.

引用

页码：277 / 282

页数：6

共 25 条

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