Mj. Garcia et al., PRACTICAL ENZYMATIC ROUTE TO OPTICALLY-ACTIVE 3-HYDROXYAMIDES - SYNTHESIS OF 1,3-AMINOALCOHOLS, Tetrahedron : asymmetry, 4(10), 1993, pp. 2199-2210
Candida antarctica lipase (CAL) is a very efficient catalyst for the e
nantioselective aminolysis of different racemic 3-hydroxyesters with a
liphatic amines. The degree of enantioselectivity exhibited by the lip
ase depends on the substrate and nucleophile, but in the most cases, t
he E values obtained are very satisfactory. CAL also catalyzes the ami
nolysis of ethyl (+/-)-3,4-epoxybutyrate and the epoxyamide was achiev
ed with high e.e. The chemical reduction of the 3-hydroxyamides obtain
ed by enzymatic aminolysis yields the corresponding 1,3-aminoalcohols.