C2-symmetric enantiopure bis-α,β-butenolides as diastereoselective substrates in ethylene photocycloaddition

被引：15

作者：

de March, P ^{[1
]}

Figueredo, M ^{[1
]}

Font, J ^{[1
]}

Raya, J ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

stereocontrol; furanones; cycloadditions;

D O I：

10.1016/S0040-4039(99)00172-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several C-2-symmetric bis-alpha,beta-butenolides have been synthesised starting from D-mannitol. Their [2+2]-photocycloaddition to ethylene has been studied as a model reaction to evaluate the influence of the protecting groups of the central diol system on the facial diastereoselectivity. The trimethylsilyl derivative shows the highest selectivity. The bis-cyclobutane containing products have been converted into the enantiopure adducts of gamma-hydroxymethyl-alpha,beta-butenolide and ethylene. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2205 / 2208

页数：4

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