STEREOSELECTIVE SYNTHESIS OF DIMETHYL-E-2-(TRIMETHYLSILYL)VINYL AND DIETHYL-E-2-(TRIMETHYLSILYL)VINYL PHOSPHONATES AND THEIR USE IN THE DIELS-ALDER REACTION

被引：8
作者：
MAFFEI, M
BUONO, G
机构：
[1] Ensspicam (Ecole Nationale Superieure de Synthèse, de Procédés et d'Ingéniérie Chimiques d'Aix Marseille), URA 1410 du CNRS, Faculté de St Jerome, Marseille Cedex 13, Avenue Escadrille Normandie Niemen
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1993年 / 79卷 / 1-4期
关键词：
VINYL PHOSPHONATES; VINYL SILANES; PALLADIUM-CATALYZED CARBON-PHOSPHORUS BOND FORMATION; DIELS-ALDER REACTION; ORGANOPHOSPHORUS DIENOPHILES; LEWIS ACIDS;
D O I：
10.1080/10426509308034422
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Dimethyl E-2-(trimethylsilyl)vinyl phosphonate 1 and diethyl E-2-(trimethylsilyl)vinyl phosphonate 2 are obtained stereoselectively by Pd (0) coupling of an E/Z mixture of (2-trimethylsilyl)vinyl bromide 3 and dimethyl phosphite or diethyl phosphite, respectively. Their use in the Diels-Alder reaction with cyclopentadiene is described, and coordination of aluminum trichloride to the phosphonyl group favors the endo stereoselectivity.
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页码：297 / 301
页数：5
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