Lipase TL®-mediated kinetic resolution of glycerol analogues: Efficient convergent route to both enantiomeric glycerol units

Abstract

In the presence of pyridine, at −5 °C, lipase TL®-mediated kinetic resolution of (±)-1-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-propan-2-ol was found to proceed efficiently to give the corresponding (S)-alcohol and (R)-acetate, each with high enantiomeric excess and in quantitative yield. The alcohol (S)-1 and the acetate (R)-2-derived alcohol, (R)-1, could be converted to the 1-protected glycerols with either of the stereochemistry by the choice of the deprotection of the protective groups.