Ag(I)-Catalyzed Kinetic Resolution of Cyclopentene-1,3-diones

Organic Letters
Hua-Chao LiuChun-Jiang Wang

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.

References

Jun 9, 2005·Angewandte Chemie·Edwin Vedejs, Mara Jure
Feb 9, 2007·Organic Letters·Lifeng Wan, Marcus A Tius
Jun 26, 2007·Chemical Reviews·Saibal DasRené Grée
Jan 16, 2008·Bioorganic & Medicinal Chemistry Letters·Vincent J SantoraAndrew J Grottick
Aug 8, 2008·Journal of Medicinal Chemistry·Chen ZhaoMarlon D Cowart
Nov 28, 2008·Journal of the American Chemical Society·Chun-Jiang WangFeng Gao
Jul 18, 2009·Journal of Natural Products·Naonobu TanakaYoshihisa Takaishi
Sep 24, 2009·Chemical Reviews·Vanya B Kurteva, Carlos A M Afonso
Jan 23, 2010·Lung Cancer : Journal of the International Association for the Study of Lung Cancer·Robert C DoebelePaul A Bunn
Jul 19, 2014·Chemical Communications : Chem Comm·Javier Adrio, Juan C Carretero
Jan 1, 2015·Journal of the American Chemical Society·Madhu Sudan Manna, Santanu Mukherjee
Feb 11, 2015·Chemical Communications : Chem Comm·S E WalkerA-L Lee
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Apr 22, 2016·Chemical Reviews·Svilen P SimeonovCarlos A M Afonso
Jun 2, 2016·Journal of the American Chemical Society·Kai-Jiong XiaoJin-Quan Yu
Jun 28, 2016·Chemical Society Reviews·A BorissovD J Dixon
Jul 8, 2016·Angewandte Chemie·Haipeng HuXiaoming Feng

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