ESTER ENOLATE CLAISEN REARRANGEMENTS OF ALLYL ALPHA-FLUOROACETATES AND ALPHA-FLUOROPROPANOATES

被引：38

作者：

WELCH, JT

PLUMMER, JS

CHOU, TS

机构：

[1] Department of Chemistry, State University of New York at Albany, Albany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期

关键词：

D O I：

10.1021/jo00001a065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ester enolate Claisen rearrangement of allyl alpha-fluoroacetates 1 forms 2-fluoroalkenoic acids 2 in good to excellent yield with good internal asymmetric induction. This selectivity was unexpected as stereoselective deprotonation of fluoroacetates is not normally possible. The selective formation of the required alpha-fluoro silyl ketene acetal 3 was found to result from the stereoselective rearrangement of the allyl alpha-fluoro-alpha-silylacetate isomer. Although silyl ketene acetals derived from alpha-fluoropropanoates 7 also rearranged, control of internal asymmetric induction was not possible.

引用

页码：353 / 359

页数：7

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