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

Article abstract of DOI:10.1016/0957-4166(95)00403-3

A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane 1 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.