Phosphonate modification for a highly (Z)-selective synthesis of unsaturated esters by Horner-Wadsworth-Emmons olefination

被引：25
|
作者：
Touchard, FP [1 ]
机构：
[1] Rhodia Rech, Ctr Rech Lyon, F-69192 St Fons, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 09期
关键词：
alkenes; olefination; wittig reaction;
D O I：
10.1002/ejoc.200400769
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Horner-Wadsworth-Emmons (HWE) reaction of various ethyl diarylphosphonoacetates with benzaldehyde, cyclohexane carboxaldehyde and octanal is reported. Selectivities of up to 98% at -78 degrees C are obtained with the three substrates. Among all the phosphonates prepared, the reagent based on 2-tert-butylphenol proved to be especially efficient, with Z/E ratios close to 95:5 at 0 degrees C. It appears thus to be the reagent of choice for the (Z)-selective HWE reaction with both aromatic and aliphatic aldehydes. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码：1790 / 1794
页数：5
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