Palladium-catalyzed synthesis of tetrahydrofurans from γ-hydroxy terminal alkenes:: Scope, limitations, and stereoselectivity

被引：87

作者：

Hay, MB ^{[1
]}

Hardin, AR ^{[1
]}

Wolfe, JP ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期

关键词：

D O I：

10.1021/jo050022+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, stereoselective synthesis of substituted tetrahydrofurans via Pd-catalyzed reactions of aryl and vinyl bromides with gamma-hydroxy terminal alkenes is described. This transformation affords trans-2,5- and trans-2,3-disubstituted tetrahydrofurans with up to > 20:1 dr. This methodology also provides access to bicyclic and spirocyclic tetrahydrofuran derivatives in good yield with 10-20:1 dr. The scope and limitations of these transformations are discussed in detail, as are the effect of substrate sterics and electronics on yield and stereoselectivity. A proposed mechanism of these transformations is presented along with a model that rationalizes the stereochemical outcome of the reactions.

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页码：3099 / 3107

页数：9

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