title: Directed nickel-catalyzed negishi cross coupling of alkyl aziridines.
abstract: Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp(3)-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition and facilitates reductive elimination. Studies pertinent to elucidation of the mechanism of cross coupling are also presented.
authors: Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
authors: Daniel K
authors: DK
authors: Nielsen
authors: Chung-Yang Dennis
authors: CY
authors: Huang
authors: Abigail G
authors: AG
authors: Doyle
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
chemical_list: D001388:Aziridines; D009532:Nickel