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Paper | Regular issue | Vol 98, No. 8, 2019, pp.1055-1073
Published online, 7th August, 2019
DOI: 10.3987/COM-19-14127
Synthesis of 8-Oxa-2-azabicyclo[3.2.1]octane Using a 1,3-Dipolar Cycloaddition Reaction

Kazuhiro Higuchi,* Yoshiki Matsubayashi, Takuma Sakurai, Motoki Ito, and Shigeo Sugiyama

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


Herein, we report the application of 1,3-dipolar cycloaddition reaction toward the synthesis of a variety of 8-oxa-2-azabicyclo[3.2.1]octane compounds, the core structure of atkamine. The target compounds were obtained using a combination of a vinyl ether and carbonylylide, which was generated from a diazo compound and rhodium catalyst, in the presence of a Lewis acid.