Regiochemical control in intramolecular cyclization of methylene-interrupted epoxydiols

被引：20

作者：

Narayan, RS

Sivakumar, M

Bouhlel, E

Borhan, B ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

[2] Univ Ctr, Fac Sci, Dept Chim, Monastir 5000, Tunisia

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 16期

关键词：

D O I：

10.1021/ol016118h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Methylene-interrupted epoxydiols have multiple regiochemical routes for cyclization. The 5-exo process is the most prevalent under acidic conditions. However, the regioselectivity can be controlled by the appropriate choice of acid promoter and pendant groups adjacent to the epoxide. The 5-exo product is obtained exclusively without the presence of a carbocation-stabilizing pendant group. Alkenyl and thiophenyl groups adjacent to the epoxide alter the regioselectivity and enable access to the 5-endo tetrahydrofuran and 6-endo tetrahydropyran products.

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收藏

页码：2489 / 2492

页数：4

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