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

…, I Schiffers, CL Dinter, A Gerlach

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

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被引用次数: 148

摘要

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 ...