A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones

被引：50

作者：

Gupta, Archana ^{[1
]}

Yadav, Veejendra K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 46期

关键词：

1,3-dipole; cycloaddition; 2,3,5-and 2,3,4,5-substituted tetrahydrofurans;

D O I：

10.1016/j.tetlet.2006.09.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and highly diastereoselective synthesis of highly substituted tetrahydrofurans from the reaction of a vicinal t-butyldiphenylsilylmethyl-substituted cyclopropyl diester with aldehydes and ketones has been developed. The 2,5-cis-disubstitution predominates over the 2,5-trans-disubstitution by as much as 12:1. The reaction with cyclic ketones generates spiro-fused tetrahydrofurans in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8043 / 8047

页数：5

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