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.
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页码：353 / 359
页数：7
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