Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds
A new facile method for monoacylation of diols has been developed. A variety of cyclic and acyclic diols, in particular 1,2-diols, were selectively monobenzoylated in good yields by the reaction with benzoyl chloride in the presence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully applied to a kinetic resolution of racemic 1-phenyl-1,2-ethanediol using a chiral organotin catalyst. The ee was dependent on the kind of base, water as an additive, and the reaction temperature.
Iwasaki
F
Tsukuba Research Laboratory, Tokuyama Corporation, 40 Wadai, Tsukuba 300-4247, Japan, Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8131, Japan, and Institute for Fundamental Research of Organic.
Maki
T
Onomura
O
Nakashima
W
Matsumura
Y