Reductive and base-induced cleavage reactions of oxabicyclic compounds

被引：31

作者：

Lautens, M

Ma, SH

机构：

[1] Department of Chemistry, University of Toronto, Toronto

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 11期

关键词：

D O I：

10.1016/0040-4039(96)00120-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-methylene-7-oxabicyclo[2.2.1]heptane 2 and 6-methylene-8-oxabicyclo[3.2.1] octanes 15 and 16 were prepared in enantiomerically enriched form, and shown to undergo a base-induced beta-elimination of the oxygen bridge leading to substituted methylenecyclohexenols and methylenecycloheptenediols. Li/NH3 induced an alpha-reduction of 7-oxabicyclo[2.2.1]heptan-2-one 1 and afforded beta-hydroxy cyclohexanone 19.

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页码：1727 / 1730

页数：4

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