Convenient synthesis of a reactive ester homoenolate

被引：16

作者：

DiMauro, E ^{[1
]}

Fry, AJ ^{[1
]}

机构：

[1] Wesleyan Univ, Dept Chem, Middletown, CT 06459 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 45期

关键词：

carbanions; fluorine; fluorine compounds; mechanisms; silicon; silicon compounds;

D O I：

10.1016/S0040-4039(99)01653-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction between methyl 3-phenyl-3-trimethylsilylpropionate (8) and catalytic quantities of tetrabutylammonium triphenyldifluorosilicate (TBAT) effects desilylation to the corresponding homoenolate, which can be trapped by a variety of electrophiles. Rearrangement of the homoenolate to the more stable enolate was not observed. The reaction amounted to overall umpolung of methyl cinnamate, the alpha,beta-unsaturated ester from which 8 was prepared. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7945 / 7949

页数：5

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