Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds

A new facile method for monoacylation of diols has been developed. A variet y of cyclic and acyclic diols, in particular 1,2-diols, were selectively mo nobenzoylated in good yields by the reaction with benzoyl chloride in the p resence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully appl ied to a kinetic resolution of racemic 1-phenyl-1,2-ethanediol using a chir al organotin catalyst. The ee was dependent on the kind of base, water as a n additive, and the reaction temperature.