GLYCOSYLIDENE CARBENES .3. SYNTHESIS OF SPIROCYCLOPROPANES

被引：22

作者：

VASELLA, A

WALDRAFF, CAA

机构：

[1] Organisch-Chemisches Institut, Universität Zürich, Zürich, CH-8057

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 03期

关键词：

D O I：

10.1002/hlca.19910740316

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermolysis of the glycosylidene-derived O-benzylated diazirine 1 in the presence of N-phenylmaleimide (2), acrylonitrile (3), dimethyl fumarate (4), or dimethyl maleate (5) led in good yields to mixtures of the spirocyclopropanes 6/7, 8-11, 12/13, and 12/13/16/17. The diastereoselectivity depends upon the alkene. The cycloaddition of 1 to 5 is not diastereospecific, in keeping with previous results. Deprotection of 12, 13, 16, and 17 yielded the tetrols 14, 15, 18, and 19, respectively.

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页码：585 / 593

页数：9

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