Practical and highly enantioselective ring opening of cyclic meso-anhydrides mediated by cinchona alkaloids

…, I Schiffers, CL Dinter, A Gerlach

Index: Bolm, Carsten; Schiffers, Ingo; Dinter, Christian L.; Gerlach, Arne Journal of Organic Chemistry, 2000 , vol. 65, # 21 p. 6984 - 6991

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Citation Number: 148

Abstract

The cinchona alkaloid-mediated opening of prochiral cyclic anhydrides in the presence of methanol leading to optically active hemiesters is described. Very structurally diverse anhydrides are converted into their corresponding methyl monoesters, and either enantiomer can be obtained with up to 99% ee by using quinine or quinidine as directing additive. After the reaction, the alkaloids can be recovered almost quantitatively and ...