Enantioselective bioreduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime)

The baker's yeast reduction of (E)-1-phenyI-1,2-alkanedione 2-(O-methyloxim e), PhC(O)C(NOMe)R (R = Me, Et, n-Pr, n-Bu), gave the corresponding optical ly active alcohols PhCH2OHC(NOMe)R in 88-99% enantiomeric excess and 48-75% chemical yield. The R configuration was proposed for these alcohols based on circular dichroism analysis. Only the phenylglyoxal O-methylaldoxime (R= H) gave poor enantiomeric excess (65%) and chemical yield (14%). These comp ounds are potential chiral building blocks for the stereoselective synthesi s of norephedrine analogs. (C) 2000 Elsevier Science Ltd. All rights reserv ed.