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New catalytic ability of copper(II) ion has been exploited for monobenzoylation of 1,2-diols. The catalyst can be readily modified by ligation to acquire higher stereoselectivity. Highly effective kinetic resolution of dl-1,2-diols was achieved. The enantiodiscrimination process was clearly shown to be controlled by the kinetics of acylation of dl-1,2-diols. The catalytic method was successfully applied to asymmetric desymmetrization of meso-hydrobenzoin.

A variety of enecarbamates and enamides were synthesized from -methoxy carbamates and -methoxy amides prepared by anodic methoxylation of amine derivatives. Some new carbon-carbon bond-forming reactions and hydroxylation at the ß position of amines have been accomplished by using these enecarbamates and enamides as key intermediates. Also, new synthetic routes of nicotinaldehyde and pyrrole derivatives have been exploited by utilizing anodic dimethoxylation of carbamates of piperidine and pyrrolidine, respectively.