title: An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.
abstract: A novel copper-catalyzed electrophilic amination of cyclopropanols with O-benzoyl-N,N-dialkylhydroxylamines to synthesize various β-aminoketones via a sequence that includes C-C bond cleavage and Csp(3)-N bond formation is reported. The reaction conditions are mild and tolerate a wide range of functional groups including benzoate, tosylate, expoxide, and α,β-unsaturated carbonyls, which are incompatible in the traditional amine nucleophilic conjugate addition and the Mannich reaction conditions. Preliminary mechanistic studies and a proposed catalytic cycle of this umpolung β-aminoketone synthesis process have been described as well.
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Zhishi
authors.initials: Z
authors.lastname: Ye
authors.affiliation: Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Mingji
authors.initials: M
authors.lastname: Dai
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000588:Amines; D004988:Ethers, Cyclic; D007659:Ketones; C043657:cyclopropanol; D003300:Copper