DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF CHIRAL 2-SUBSTITUTED-1,3-DIENES

被引：19

作者：

BLOCH, R

CHAPTALGRADOZ, N

机构：

[1] Laboratoire des Carbocycles, associé au CNRS, Institut de Chimie Moléculaire d'Orsay, 91405 Orsay

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 41期

关键词：

CYCLOADDITION; REGIOSELECTIVITY; PI-FACIAL SELECTIVITY; CHLOROPRENE;

D O I：

10.1016/S0040-4039(00)60028-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from chloroprene, an improved synthesis of alkyl and aryl (1,3-butadien-2-yl) methanols 1 is described. Thermal Diels-Alder reactions between these dienols or their ethers 3 and various dienophiles give rise with fair to good regio- and diastereoselectivity to monocyclic "para" adducts. In contrast a total regioselectivity and an excellent pi-facial selectivity is observed when the Diels-Alder cycloadditions of the dienic ethers 3 are conducted in the presence of a Lewis acid.

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页码：6147 / 6150

页数：4

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