Practical Enzymatic Route to Optically Active 3-Hydroxyamides. Synthesis of 1,3-Aminoalcohols

Article abstract of DOI:10.1016/S0957-4166(00)80070-1

Candida antarctica lipase (CAL) is a very efficient catalyst for the enantioselective aminolysis of different racemic 3-hydroxyesters with aliphatic amines.The degree of enantioselectivity exhibited by the lipase depends on the substrate and nucleophile, but in the most cases, the E values obtained are very satisfactory.CAL also catalyzes the aminolysis of ethyl (+/-)-3,4-epoxybutyrate and the epoxyamide was achieved with high e. e.The chemical reduction of the 3-hydroxyamides obtained by enzymatic aminolysis yields the corresponding 1,3-aminoalcohols.