title: Tin-free radical addition of acyloxymethyl to imines.
abstract: Acyloxymethyl radicals were generated from the corresponding iodomethyl esters and successfully underwent addition to the CN bond of N-Ts, N-PMP, and N-Dpp imines by the action of dimethylzinc or triethylborane. Ethyl acetate, toluene, and benzene as well as dichloromethane were suitable solvents. The utility of acyloxymethyl radicals as a hydroxymethyl anion equivalent was highlighted by the facile hydrolysis of the acyloxy moiety of the adducts to give the corresponding amino alcohol derivatives in good to high yield.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Mayu
authors.initials: M
authors.lastname: Nakano
authors.forename: Masaru
authors.initials: M
authors.lastname: Maekawa
authors.forename: Tito
authors.initials: T
authors.lastname: Akindele
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D005609:Free Radicals / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D004952:Esters; D005609:Free Radicals; D006847:Hydrocarbons, Iodinated; D007097:Imines; D009942:Organometallic Compounds; C511262:dimethylzinc