Oxonia-cope rearrangement and side-chain exchange in the prins cyclization

被引：155

作者：

Crosby, SR

Harding, JR

King, CD

Parker, GD

Willis, CL

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 04期

关键词：

D O I：

10.1021/ol0102850

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.

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页码：577 / 580

页数：4

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