Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane

A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane1 by lipase has been developed. The transesterification of (±)?1 with vinyl acetate in the presence of Lipase AK without solvent proceeded to give (+)?1 and the corresponding acetate (+)?5 in good yield and high enantiomeric ratio. The alcohol (+)?1 was transformed to the optically active hydantoins 12 and 13, possible intermediates for the synthesis of conformational constrained analogues of AP-5.