Asymmetric oxidation of 1,2-diols, aminoalcohols and aminoaldehydes in the presence of copper(II) triflate and (R,R)-Ph-BOX, was accomplished by electrochemical method using Bras a mediator. This oxidation was applicable to kinetic resolution of racemic cis-cycloalkane-1,2-diols, aminoalcohols and aminoaldehydes to afford optically active compounds with good to high enantioselectivity.

Abstract-A convenient method for synthesis of optically active azetidin-2-ones using electrochemical oxidation has been exploited. The method consists of a diastereoselective intramolecular C-C bond forming reaction between active methylene and methyne groups through an electrochemical system in which positive iodine species acted as mediators under mild conditions.

A diastereodivergent synthesis of N-substituted iminolactones by bromoiminolactonization of α-substituted α-allylmalonamides is reported. Whereas bromocyclization under conventional chemical conditions provided cis-bromoiminolactones, electrochemical conditions exhibited complementary diastereoselectivity to afford the trans-products. A variety of substituents on the nitrogen atoms and an α-position of the malonamide were tolerated under both sets of conditions to afford the corresponding iminolactones in excellent yields and high diastereoselectivities.

Selective recognition: The first efficient method for the kinetic resolution of racemic amino aldehydes (see scheme, PG=protecting group) is based on a copper(II)/(R,R)‐Ph‐BOX complex. The coordinated amino aldehydes were transformed into optically active amino acid methyl esters, and the non‐coordinated amino aldehydes were converted into optically active amino aldehyde dimethyl acetals.

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