Asymmetric synthesis of tropanes by rhodium-catalyzed [4+3] cycloaddition

被引：137

作者：

Reddy, Ravisekhara P. ^{[1
]}

Davies, Hum M. L. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 34期

关键词：

D O I：

10.1021/ja072936e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rhodium-catalyzed [4 + 3] cycloaddition between methyl 2-(siloxy)vinyldiazoacetate and pyrroles results in the enantioselective synthesis of highly functionalized 8-azabicyclo[3.2.1]octa-2,6-dienes (tropanes). The reaction proceeds via a rhodium-carbenoid intermediate and involves a tandem cyclopropanation/Cope rearrangement mechanism. The optimum chiral dirhodium catalyst for this transformation is the adamantyl glycine-derived complex, Rh-2(S-PTAD)(4).

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页码：10312 / +

页数：3

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