Tin-free radical addition of acyloxymethyl to imines.
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.
Yamada
Ken-ichi
K
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Nakano
Mayu
M
Maekawa
Masaru
M
Akindele
Tito
T
Tomioka
Kiyoshi
K
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*
D000605:Amino Alcohols; D004952:Esters; D005609:Free Radicals; D006847:Hydrocarbons, Iodinated; D007097:Imines; D009942:Organometallic Compounds; C511262:dimethylzinc