Highly selective resolution of secondary alcohols and acetoacetates with lipases and diketene in organic media

Article abstract of DOI:10.1016/0957-4166(96)00121-8

By the catalysis of lipases, racemic 1-phenylethanol 1a is reacted with diketene in isopropyl ether at room temperature to give (S)-1a (R¹ = Me, R² = Ph, 36%, 99% ee) and (R)-1-phenylethyl acetoacetate 2a (51%, 77% ee). The strategy was also successfully applied to racemic 1-(1-naphthyl)ethanol 1b, 1-(2-naphthyl)ethanol 1c, 1-phenyl-2-propanol 1d, 1,2,3,4-tetrahydro-1-naphthol 1e, and 2-octanol 1f with high E-values up to > 100.