Palladium catalyzed kinetic and dynamic kinetic asymmetric transformations of γ-acyloxybutenolides. Enantioselective total synthesis of (+)-aflatoxin B1 and B2a

BM Trost, FD Toste

Index: Trost, Barry M.; Toste, F. Dean Journal of the American Chemical Society, 2003 , vol. 125, # 10 p. 3090 - 3100

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Citation Number: 85

Abstract

The reaction of γ-tert-butoxycarbonyloxy-2-butenolide with phenol nucleophiles in the presence of a Pd (0) complex with chiral ligands may be performed under conditions that favor either a kinetic resolution or a kinetic asymmetric transformation (KAT) or dynamic kinetic asymmetric transformation (DYKAT). Performing the reaction at high concentration (0.5 M) in the presence of a carbonate base favors the former, ie, KAT; whereas, running ...