Desymmetrisation of 4, 4-disubstituted cyclohexanones by enzyme-catalysed resolution of their enol acetates

…, AJ Carnell, MLE Hernandez, A Pettman

文献索引：Allan, Graham; Carnell, Andrew J.; Hernandez, Maria Luisa Escudero; Pettman, Alan Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 20 p. 3382 - 3388

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被引用次数: 11

摘要

Enol acetates 3–10 derived from prochiral 4, 4-disubstituted cyclohexanones can be resolved with Pseudomonas fluorescens lipase to give enantiomerically pure (> 99% ee) enol esters by transesterification with n-BuOH. The product ketones are prochiral and can easily be recycled giving an overall desymmetrisation of the ketone. Highest selectivity was obtained for substrates containing a 4-cyano and 4-aryl or a 4-benzyloxy substituent. The ...