Cyclic trans-β-amino alcohols: preparation and enzymatic kinetic resolution

Enantioenriched cyclic beta-amino alcohols, trans-2-aminocyclohexanols (ee, > 99%), trans-2-aminocyclopentanols (ee, > 99%), trans-1-amino-2-indanols (ee, > 99%) and trans-2-amino-1-indanols (ee, similar to 98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution. (C) 2011 Elsevier Ltd. All rights reserved.