Enzymatic synthesis of optically active trifluoromethylated 1- and 2-hydroxyalkanephosphonates

Convenient enzymatic methods have been developed for the preparation of chiral 1- and 2-hydroxyalkanephosphonates bearing a trifluoromethyl moiety with high enantiomeric excess via Candida antarctica lipase B-, Mucor miehei lipase-catalyzed alcoholysis and C. rugosa lipase-catalyzed hydrolysis in organic media. The enantiomeric excess of such trifluoromethylated carbinols was determined using quinine as a chiral solvating agent. The catalytic preference was assigned according to the Kusumi–Ohtani method.