title: Asymmetric Electrophilic α-Amination of Silyl Enol Ether Derivatives via the Nitrosocarbonyl Hetero-ene Reaction.
abstract: The first example of a general asymmetric nitrosocarbonyl hetero-ene reaction is described. The procedure uses a copper-catalyzed aerobic oxidation of a commercially available chiral nitrosocarbonyl precursor (EleNOr) and is operationally simple. The transformation is both high yielding and highly diastereoselective for a range of silyl enol ether derivatives. A variety of synthetically useful postfunctionalization reactions are presented along with a mechanistic rationale that can be used as a predictive model for future asymmetric reactions with nitrosocarbonyl intermediates.
authors: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors: David
authors: D
authors: Sandoval
authors: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors: Andrey V
authors: AV
authors: Samoshin
authors: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors: Javier
authors: J
authors: Read de Alaniz
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004987:Ethers; D009603:Nitroso Compounds; D017646:Organosilicon Compounds; D003300:Copper