Stereoselective Synthesis of α-fluoro-β-trifluoromethyl-α,β-unsaturated Esters by Horner-Wadsworth-Emmons Coupling

被引：2

作者：

Landge, Shainaz M. ^{[1
,2
]}

Toeroek, Bela ^{[1
]}

机构：

[1] Univ Massachusetts, Dept Chem, Boston, MA 02125 USA

[2] Georgia So Univ, Dept Chem, Statesboro, GA 30460 USA

来源：

LETTERS IN ORGANIC CHEMISTRY | 2014年 / 11卷 / 05期

关键词：

alpha-fluoro-beta-trifluoromethyl-alpha-beta-unsaturated esters; Horner-Wadsworth-Emmons coupling; trifluoromethyl ketones; FLUORINATED ANALOGS; ACID-ESTERS; TRIFLUOROACETALDEHYDE; HYDROXYALKYLATION; INHIBITOR; INDOLES;

D O I：

10.2174/1570178611666140124001052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Fluoro-beta-trifluoromethyl-alpha,beta-unsaturated esters were synthesized via the reaction of diethyl (1-fluoro-1-carbethoxymethyl) phosphonate with a variety of aromatic/heterocyclic trifluoromethyl ketones and trifluoroacetaldehyde ethyl hemiacetal by the Horner-Wadsworth-Emmons (HWE) coupling. The effect of base, solvent, as well as reactant ratio has been investigated. The present method is highly stereoselective, attractive and convenient for the synthesis of the target compounds due to the availability of the reagents, simplicity of the approach and good yields of the products.

引用

页码：374 / 379

页数：6

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