Preparation and lipase-catalyzed enantiotope selective acetylation of the prochiral 2-acyloxypropane-1,3-diols (1a-h) including sulfonic ester (1a- c) and carboxylic ester (1d-h) series is described. A strong influence of the acyl moiety in these diols on the enantiotope selectivity of the porcine pancreatic lipase (PPL)-catalyzed reaction with vinyl acetate was observed. The best results were achieved with the 2-(4-methylbenzoyl)oxy- and cyclohexanecarbonyloxypropane-1,3-diols (1g and 1h) resulting in acetylated products (2g) of ≥ 98% e.e. in 77% yield and (2h) of 95% e.e. in 66% yield, respectively. (C) 2000 Elsevier Science B.V.
- Enzymes and enzyme reactions
- Substituent effects
ASJC Scopus subject areas
- Process Chemistry and Technology