Diels− Alder Cycloaddition Strategy for Kinetic Resolution of Chiral Pyrazolidinones

MP Sibi, K Kawashima, LM Stanley

Index: Sibi, Mukund P.; Kawashima, Keisuke; Stanley, Levi M. Organic Letters, 2009 , vol. 11, # 17 p. 3894 - 3897

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Citation Number: 19

Abstract

A rare example of the application of a catalytic, enantioselective Diels− Alder cycloaddition to affect a kinetic resolution has been developed. Chiral pyrazolidinones are resolved with high selectivity through a process that utilizes a relay of stereochemical information from a permanent chiral center to a fluxional chiral center to enhance the inherent selectivity of the chiral Lewis acid catalyst.