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铑(I)催化的1-(1-炔基)环丙基酮的区域和立体特异性羰基化反应:一种合成高度取代的5,6-二氢环戊并[c]呋喃-4-酮的模块化方法。

Rh(I)-catalyzed regio- and stereospecific carbonylation of 1-(1-alkynyl)cyclopropyl ketones: a modular entry to highly substituted 5,6-dihydrocyclopenta[c]furan-4-ones.

作者信息

Zhang Yanqing, Chen Zuliang, Xiao Yuanjing, Zhang Junliang

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.

出版信息

Chemistry. 2009;15(21):5208-11. doi: 10.1002/chem.200900413.

Abstract

Efficient route: A novel Rh(I)-catalyzed regio- and stereospecific carbonylation reaction of (1-alkynyl)cyclopropyl ketones by selective activation of a carbon-carbon sigma bond of the cyclopropane ring was demonstrated (see scheme). This method provides a general, efficient, stereoselective route to synthesise 1,3,5-trisubstituted and 1,3,5,6-tetrasubstituted 5,6-dihydrocyclopenta[c]furan-4-one with convertible functional groups.

摘要

高效路线

通过环丙烷环碳-碳σ键的选择性活化,展示了一种新型铑(I)催化的(1-炔基)环丙基酮的区域和立体特异性羰基化反应(见方案)。该方法提供了一条通用、高效、立体选择性的路线,用于合成具有可转化官能团的1,3,5-三取代和1,3,5,6-四取代的5,6-二氢环戊并[c]呋喃-4-酮。

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