Alkylation of magnesium enamide with alkyl chlorides and fluorides.
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.
Hatakeyama
Takuji
T
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Ito
Shingo
S
Nakamura
Masaharu
M
Nakamura
Eiichi
E
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
D000577:Amides; D006843:Hydrocarbons, Chlorinated; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D008274:Magnesium