title: Copper(II) triflate catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds.
abstract: A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)(2) + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI═NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
authors.forename: Thi My Uyen
authors.initials: TM
authors.lastname: Ton
authors.forename: Ciputra
authors.initials: C
authors.lastname: Tejo
authors.forename: Diane Ling Ying
authors.initials: DL
authors.lastname: Tiong
authors.forename: Philip Wai Hong
authors.initials: PW
authors.lastname: Chan
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D010618:Phenanthrolines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001388:Aziridines; D010618:Phenanthrolines; D003300:Copper; C025205:1,10-phenanthroline