title: Alkylation of magnesium enamide with alkyl chlorides and fluorides.
abstract: A magnesium enamide derived from N-2-(N',N'-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an alpha-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.
authors.affiliation: Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Takuji
authors.initials: T
authors.lastname: Hatakeyama
authors.forename: Shingo
authors.initials: S
authors.lastname: Ito
authors.forename: Masaharu
authors.initials: M
authors.lastname: Nakamura
authors.forename: Eiichi
authors.initials: E
authors.lastname: Nakamura
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D006843:Hydrocarbons, Chlorinated; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D008274:Magnesium