Accounts of Chemical Research 2004-08-01

Asymmetric organic catalysis with modified cinchona alkaloids.

Shi-Kai Tian, Yonggang Chen, Jianfeng Hang, Liang Tang, Paul McDaid, Li Deng

Index: Acc. Chem. Res. 37(8) , 621-31, (2004)

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Abstract

Insights into the role played by modified cinchona alkaloids in the Sharpless asymmetric dihydroxylation inspired studies of modified cinchona alkaloids as chiral organic catalysts that lead to the development of highly enantioselective alcoholyses for the desymmetrization, kinetic resolution, and dynamic kinetic resolution of cyclic anhydrides, cyanation of ketones, and 1,4-addition of thiols to cylic enones. These studies demonstrate the potential of modified cinchona alkaloids as broadly useful chiral organic catalysts for asymmetric synthesis.