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Ag(I)-Catalyzed Kinetic Resolution of Cyclopentene-1,3-diones
Hua-Chao Liu1, Liang Wei1, Rong Huang1
1College of Chemistry and Molecular Sciences , Wuhan University , Wuhan 430072 , China.
Abstract:
An efficient kinetic resolution of readily available racemic cyclopentene-1,3-diones has been developed via a Ag(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides. This methodology shows good functional-group tolerance, delivering an array of synthetically valuable cyclopentene-1,3-diones with excellent stereoselectivity and generally high resolution efficiency ( s = 48-226) accompanied by the biologically important fused pyrrolidine derivatives. Notably, this strategy allows facile access to the key intermediates for the synthesis of (+)-madindolines A and B.
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