Studies of chemoselectivity in Diels-Alder reactions of 2-(p-tolylsulfinyl)-1,4-benzoquinone and styrenes:: Formation of (p-tolylsulfinyl)-1,4-phenanthrenequinones

被引：5

作者：

Carreño, MC ^{[1
]}

Urbano, A ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ C 1, Madrid 28049, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期

关键词：

cycloadditions; quinones; sulfoxides; chemoselectivity;

D O I：

10.1016/S0040-4039(00)00593-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of 2-(p-tolylsulfinyl)-1,4-benzoquinone 1 with 4-methoxystyrenes 2a-b in polar solvents afforded 2- and 3-(p-tolylsulfinyl)-1,4-phenanthrenequinones 4a-b and 5a-b as major compounds. A second cycloaddition of 5a and 4a with 3,4-dimethoxystyrene 2a gave access to C- and S-shaped pentacyclic molecules 10 and 11 in a highly regioselective way. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4117 / 4121

页数：5

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