A new synthesis of spiroketals via sulfonyl-substituted dihydropyrans

被引：5

作者：

Craig, DC ^{[1
]}

Edwards, GL ^{[1
]}

Sinclair, DJ ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON | 2001年 / 57卷 / 03期

基金：

澳大利亚研究理事会;

关键词：

oxygen heterocycles; spiro compounds; stereochemistry; sulfones;

D O I：

10.1016/S0040-4020(00)01026-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6,6- and 6,5-Spiroketals were prepared in good overall yields by alkylation and epoxide-opening reactions of 3,4-dihydro-6[(para-toluenesulfonyl)methyl]-2H-pyran (1) and subsequent acid catalysed cyclisation. The diastereoselectivity of the cyclisations was determined by a combination of 2D-NMR spectroscopy and X-ray crystallography. Attempted preparation of a 7,6-spiroketal using the same methodology was unsuccessful. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：563 / 570

页数：8

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