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  • Title: Tin-free radical addition of acyloxymethyl to imines.
    Author: Yamada K, Nakano M, Maekawa M, Akindele T, Tomioka K.
    Journal: Org Lett; 2008 Sep 04; 10(17):3805-8. PubMed ID: 18666775.
    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.
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