Unusual and efficient (Z)-stereoselective Peterson synthesis of 2-diethoxyphosphonyl-1-alkoxy-3-methylpenta-1,3-dienes. Their use in the Diels-Alder reaction.

被引：17

作者：

AlBadri, H

AboutJaudet, E

Collignon, N

机构：

[1] INSA,LAB COMPOSES ORGANOPHOSPHORES,F-76131 MONT ST AIGNAN,FRANCE

[2] IRCOF,F-76131 MONT ST AIGNAN,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

关键词：

D O I：

10.1016/0040-4039(96)00452-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithiated anion of diethyl alpha-trimethylsilyl-prenylphosphonate, readily in situ generated from diethyl prenylphosphonate, reacts smoothly with various alkyl formates to give the title compounds with exclusive 1-(Z)-geometry and in high isolated yield. The [4 + 2] cycloaddition reaction of dienes 3 with electron-deficient dienophiles is described. (C) 1996 Published by Elsevier Science Ltd

引用

页码：2951 / 2954

页数：4

共 17 条

[1]

ALBADRI H, 1994, SYNTHESIS-STUTTGART, P1072

[2]

ALBADRI H, 1995, SYNTHESIS-STUTTGART, P1401

[3] NEW AND EFFICIENT SYNTHESIS OF E-4-DIETHOXYPHOSPHONYL-2-METHYL-2-BUTENAL AND OF ETHYL E-4-DIETHOXYPHOSPHONYL-2-METHYL-2-BUTENOATE, IMPORTANT BUILDING-BLOCKS IN RETINOID CHEMISTRY [J].