Resolution of racemic 3-aryloxy-1-nitrooxypropan-2-ols by lipase-catalyzedenantioselective acetylation

Both (R)- and (S)-enantiomers of 3-aryloxy-1-nitrooxypropan-2-ols (R)-(-)-1 , (S)-(+)-2 were prepared in high enantiomeric excess by lipase from Pseudo monas cepacia (Amano PS) or Pseudomonas fluorescens (Amano AK)-catalyzed ac etylation of racemic alcohols la-g with vinyl acetate in n-hexane at 4 or 2 2 degreesC. The enantio selectivity of this transformation was dependent on the substitution pattern of the aryl ring with E-values ranging from 31 to 111. (C) 2001 Elsevier Science Ltd. All rights reserved.