Asymmetric synthesis of 2,3-dihydrofurans by reaction of rhodium-stabilized vinylcarbenoids with vinyl ethers

被引：93

作者：

Davies, HML ^{[1
]}

Ahmed, G ^{[1
]}

Calvo, RL ^{[1
]}

Churchill, MR ^{[1
]}

Churchill, DG ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 08期

关键词：

D O I：

10.1021/jo972189b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II) octanoate catalyzed decomposition of 2-diazo-3-siloxybutenoates, containing (R)-pantolactone as a chiral auxiliary, in the presence of vinyl ethers results in the diastereoselective synthesis of cyclopropanes with high asymmetric induction. Treatment of the cyclopropanes with tetrabutylammonium fluoride results in desilylation and ring expansion of the resulting acylcyclopropanes to 2,3-dihydrofurans with retention of stereochemistry.

引用

页码：2641 / 2645

页数：5

共 32 条

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