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...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-02, Vol.65 (4), p.996-1002
Main Authors: Iwasaki, Fumiaki, Maki, Toshihide, Onomura, Osamu, Nakashima, Waka, Matsumura, Yoshihiro
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991394j