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J Org Chem. 2005 Apr 15;70(8):3324-7.

Triethylborane-induced intermolecular radical addition to ketimines.

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1
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

Abstract

The intermolecular carbon radical addition to ketimines was investigated by using triethylborane as a radical initiator. The screening of reactive radical acceptors showed that pyruvic hydrazone 3 and isatin hydrazone 7 exhibit good reactivities toward nucleophilic alkyl radicals. The reaction of 3 and 7 proceeded effectively even under aqueous-medium reaction conditions. In the presence of BF(3).OEt(2), the radical addition to chiral ketimine 11 proceeded with good diastereoselectivities.

PMID:
15823008
DOI:
10.1021/jo050135t
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