Approach to highly enantiopure beta-amino acid esters by using lipase catalysis in organic media

Ethyl esters often alicyclic beta-aminocarboxylic acids were resolved by lipase catalysis in organic solvents. The resolution was based on acylation of the amino group at the R-stereogenic centre with various 2,2,2-trifluoroethyl esters. An increase in the hydrophobic nature of the acyl donor enhanced the enantioselectivity and reactivity in the case of lipase SP 526 from Candida antarctica, while the opposite effect was observed with lipase PS from Pseudomonas cepacia. An unexceptional enantioselectivity enhancement was observed when 2,2,2-trifluoroethyl chloroacetate was used in the case oflipase PS catalysis. Copyright (C) 1996 Elsevier Science Ltd