Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

被引：51

作者：

Hanaki, N ^{[1
]}

Link, JT ^{[1
]}

MacMillan, DWC ^{[1
]}

Overman, LE ^{[1
]}

Trankle, WG ^{[1
]}

Wurster, JA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991315q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

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页码：223 / 226

页数：4

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