PPL-catalyzed enzymatic asymmetrization of a 2-substituted prochiral 1,3-diol with remote chiral functionality: Improvements toward synthesis of the eutomers of SCH 45012

Article abstract of DOI:10.1016/0040-4039(94)88071-9

Porcine pancreatic lipase (PPL) catalysis has been used to establish both stereocenters of the cis-(tetrahydrofuranylmethyl) tosylate 4. In addition to the enzymatic differentiation of the hydroxyl groups of the pro-chiral 1,3-diol segment of 2, successful enzymatic resolution of the racemic diol 10 provided an alternate route to the important precursor 1.