Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and -cycloheptanols

Extensive lipase screening was performed in relation to the asymmetric acet ylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozy m 435-catalysed resolutions of compounds 1-5 were based on asymmetric acyla tion of the secondary OH group at the R-stereogenic centre with various vin yl eaters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly aff ected by the size of the alicyclic ring, and by the solvent. (C) 1999 Elsev ier Science Ltd. All rights reserved.