Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds

Thi My Uyen Ton, Fanny Himawan, Joyce Wei Wei Chang, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

20 Citations (Scopus)

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=NSO2Ar 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.

Original languageEnglish
Pages (from-to)12020-12027
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number38
DOIs
Publication statusPublished - 17 Sep 2012
Externally publishedYes

Keywords

  • amination
  • copper
  • dicarbonyl compounds
  • homogenous catalysis
  • iminoiodanes

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