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Paper | Special issue | Vol 54, No. 2, 2001, pp.747-755
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8965
Regioselective Synthesis of Bridged Azabicyclic Compounds Using Radical Translocation/Cyclization Reactions of 4-Alkynyl-1-(o-iodobenzoyl)piperidines

Tatsunori Sato, Kazuya Okamoto, Yûko Nakano, Jun'ichi Uenishi, and Masazumi Ikeda*

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan


Bu3SnH-mediated radical translocation/cyclization reactions of 4-alkynyl-1-(o-iodobenzoyl)piperidines were examined. The 4-[3-(trimethylsilyl)-prop-2-ynyl]- (12) and 4-[4-(trimethylsilyl)but-3-ynyl]piperidine derivatives (16), upon treatment with Bu3SnH in the presence of azobisisobutyronitrile in boiling toluene, gave the isomeric 2-azabicyclo[3.2.1]octanes (17a,b) (34 and 51% yields, respectively) and 2-azabicyclo[3.3.1]nonane (morphan) (22) (20% yield as a diastereomeric mixture), respectively.