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.

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.

Trennung geglückt: Die erste effiziente Methode zur kinetischen Racematspaltung racemischer Aminoaldehyde (siehe Schema) beruht auf einem Kupfer(II)/(R,R)‐Ph‐BOX‐Komplex. Die koordinierten Aminoaldehyde werden dabei in optisch aktive Aminosäuremethylester überführt und die nichtkoordinierten Aminoaldehyde in optisch aktive Aminoaldehyddimethylacetale.

Enantioselective syntheses O 0031 Efficient Kinetic Resolution of Racemic Amino Aldehydes by Oxidation with N-Iodosuccinimide. -The aldehydes are efficiently resolved by treatment with NIS and Cu(II)/(R,R)-Ph-box as catalyst in MeOH into optically active amino acid methyl esters and amino aldehyde dimethyl acetals. -(MINATO, D.; NAGASUE, Y.; DEMIZU, Y.; ONOMURA*, O.; Angew. Chem., Int. Ed. 47 (2008) 49, 9458-9461; Grad. Sch. Biomed. Sci., Nagasaki Univ., Nagasaki 852, Japan; Eng.) -Klein 14-025

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