PPL-CATALYZED RESOLUTION OF 1,2- AND 1,3-DIOLS IN METHYL PROPIONATE AS SOLVENT. AN APPLICATION OF THE TANDEM USE OF ENZYMES.

Article abstract of DOI:10.1016/S0040-4020(01)89742-8

The Porcine Pancreatic Lipase (PPL)-catalyzed transesterification of 1-phenyl-1,2-ethanediol 1, 2-phenyl-1,2-propanediol 2, 1,2-decanediol 3, 1,2-pentanediol 4, 1,2-butanediol 5, 1,2-propanediol 6 and 1,3-butanediol 7 in methyl propionate as solvent was evaluated.In all substrates, the primary hydroxy group is esterified exclusively.The enantioselectivity displayed in this PPL-catalyzed reaction is moderate.The enantiomeric excess of diol (-)-1 is enhanced by subjecting propionate (-)-8, with a moderate ee (obtained by a PPL-catalyzed esterification of racemic 1 in methyl propionate), to an enzyme-catalyzed hydrolyis (tandem principle).