HIGHLY SELECTIVE GENERATION AND APPLICATION OF (E)-SILYL AND (Z)-SILYL KETENE ACETALS FROM ALPHA-HYDROXY ESTERS

被引：44

作者：

HATTORI, K ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 20期

关键词：

D O I：

10.1021/jo00072a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the stereoselective synthesis of silyl ketene acetals from a-hydroxy esters is described. Internal quench with excess TMSCI of the lithium enolate at -100-degrees-C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal. In contrast, the deprotonation at -100-degrees-C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively. The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.

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页码：5301 / 5303

页数：3

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