Highly diastereoselective synthesis of tetrahydrofurans via lewis acid-catalyzed cyclopropane/aldehyde cycloadditions

被引：132

作者：

Pohlhaus, PD ^{[1
]}

Johnson, JS ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 03期

关键词：

D O I：

10.1021/jo048230+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-step procedure for the preparation of 2,5-disubstituted tetrahydrofurans from donor-acceptor cyclopropanes and aldehydes has been developed. In the presence of a catalytic amount of Sn(OTf)(2), cyclopropanes bearing an aryl or conjugated donor substituent vicinal to a malonyl diester group undergo cycloadditions with diverse conjugated aldehydes furnishing tetrahydrofurans with high cis diastereoselectivity. This method is useful for the preparation of regiodefined tetrahydrofurans.

引用

页码：1057 / 1059

页数：3

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