Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media

Abstract 2-Aryloxy-1-propanols, primary alcohols with an oxygen atom at the stereocenter, were resolved with good to high enantioselectivity by acylation with vinyl butanoate mediated by Pseudomonas sp. lipase in di- iso -propyl ether. Potential factors affecting the enantioselectivity of the enzymatic acylation were examined: solvents, acyl donors and temperature. Using this enantioselective acylation procedure, enantiomerically pure ( R )-2-(4-chlorophenoxy)-1-propanol was prepared on a gram scale.