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.
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收藏
页码：1057 / 1059
页数：3
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