A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones

被引：63

作者：

Hata, H

Kobayashi, T

Amii, H

Uneyama, K ^{[1
]}

Welch, JT

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

[2] SUNY Albany, Dept Chem, Albany, NY 12222 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 35期

关键词：

fluorine and compounds; magnesium; cleavage reaction; aldols; enones;

D O I：

10.1016/S0040-4039(02)01343-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Flu oro-alpha,beta-unsaturated ketones were prepared from trifluoromethyl ketones via a sequence involving Mg metal promoted successive double defluorination. Trifluoromethyl ketones were transformed to beta,beta-difluoroenol silyl ethers which were then coupled with aldehydes and ketones to beta-hydroxy-alpha,alpha-difluoroketones. A second Mg-promoted defluorination of the hydroxyketones followed by acid-catalyzed hydrolysis of gamma-hydroxy-beta-fluoroenol silyl ethers provided alpha-fluoro-alpha,beta-unsaturated ketones as a final product. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：6099 / 6102

页数：4

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