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Copper(II) Triflate Catalyzed Amination of 1,3‐Dicarbonyl Compounds
Author(s) -
Ton Thi My Uyen,
Himawan Fanny,
Chang Joyce Wei Wei,
Chan Philip Wai Hong
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201219
Subject(s) - nitrene , chemistry , trifluoromethanesulfonate , amination , catalysis , lewis acids and bases , enantioselective synthesis , adduct , copper , substrate (aquarium) , medicinal chemistry , organic chemistry , metal , polymer chemistry , combinatorial chemistry , oceanography , geology
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 PhINSO 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.