Asymmetric synthesis of cyclopentenes by [3+2] annulations between vinylcarbenoids and vinyl ethers

被引：45

作者：

Davies, HML ^{[1
]}

Kong, N ^{[1
]}

Churchill, MR ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 19期

关键词：

D O I：

10.1021/jo980738n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium N-(dodecylbenzenesulfonyl)prolinate [(Rh-2(S-DOSP)(4) (1)]-catalyzed decomposition of diazobutenoates in the presence of vinyl ethers results in highly diastereoselective and enantioselective synthesis of donor/acceptor-substituted vinylcyclopropanes. Diethylaluminum chloride-induced rearrangement of these vinylcyclopropanes results in the formation of cyclopentenes with excellent control of diastereoselectivity and for the fused cyclopentenes good control of absolute stereochemistry. This study illustrates the synthetic utility of Rh-2(S-DOSP)(4) as a chiral catalyst for vinylcarbenoid cyclopropanations and the remarkable diastereocontrol that is possible in the diethylaluminum chloride-induced ring expansion of donor/acceptor-substituted vinylcyclopropanes.

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页码：6586 / 6589

页数：4

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