Scope and limitations of the Julia-Kocienski reaction with fluorinated sulfonylesters

被引：41

作者：

Calata, Charlene ^{[1
]}

Catel, Jean-Marie ^{[1
]}

Pfund, Emmanuel ^{[1
]}

Lequeux, Thierry ^{[1
]}

机构：

[1] Univ Caen Basse Normandie, ENSICAEN, CNRS, Lab Chim Mol & Thioorgan,UMR 6507,FR 3038, F-14050 Caen, France

来源：

TETRAHEDRON | 2009年 / 65卷 / 20期

关键词：

Julia-Kocienski reaction; Fluoroalkenes; Fluorinated alkylsulfones; Decarbethoxylation; HIGH-YIELD SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIPEPTIDE ISOSTERES; ALPHA-FLUORO-ALPHA; BETA-UNSATURATED ESTERS; DIASTEREOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITY; RETINOIC ACIDS; OLEFINATION; SULFONES; SUBSTRATE;

D O I：

10.1016/j.tet.2009.03.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Study of the Julia-Kocienski reaction between fluorinated arylsulfone and ketones is described. The corresponding fluoroalkenes were isolated in Moderate to good yields from beta- and delta-substituted cyclic ketones. From acyclic ketones and alpha-substituted cyclic ketones a decarbethoxylation reaction of the sulfonylesters occured. This decarbethoxylation reaction opened a new route for the preparation of a variety of fluoroalkylsulfones as potential building blocks for the preparation of fluoroalkenes. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：3967 / 3973

页数：7

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