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Tin-Free Radical Addition of Acyloxymethyl to Imines

Ken-ichi Yamada, Mayu Nakano, Masaru Maekawa, Tito Akindele and Kiyoshi Tomioka

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email:

K.-i. Yamada, M. Nakano, M. Maekawa, T. Akindele, K. Tomioka, Org. Lett., 2008, 10, 3805-3808.

DOI: 10.1021/ol8014978


Acyloxymethyl radicals, that add to imines, were generated from the corresponding iodomethyl esters by the action of dimethylzinc or triethylborane. A facile hydrolysis of the acyloxy moiety of the adducts gave the corresponding amino alcohols in good yield.

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Key Words

1,2-amino alcohols, radical reactions, pivalates, benzoates

ID: J54-Y2008-2370