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  • Title: Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds.
    Author: Ton TM, Himawan F, Chang JW, Chan PW.
    Journal: Chemistry; 2012 Sep 17; 18(38):12020-7. PubMed ID: 22890890.
    Abstract:
    A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)(2)+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO(2) Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine.
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