Grob fragmentation of 2-azabicyclo[2.2.2]oct-7-ene: tool for the stereoselective synthesis of polysubstituted piperidines.

Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal QC H3C 3J7, Canada.

The Journal of organic chemistry 2012 Jul 6

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The Grob fragmentation of azabicyclo[2.2.2]octene leads to a dihydropyridinium intermediate. This highly reactive species reacts with a variety of organocuprates and other soft nucleophiles in a regioselective manner, allowing for the rapid and stereoselective synthesis of 2,3,4-trisubstituted 1,2,3,4-tetrahydropyridines. The resulting products were either reduced in situ to the corresponding piperidine or used to achieve the stereoselective construction of various nitrogen heterocycles.

Citation

Gérald Lemonnier, André B Charette. Grob fragmentation of 2-azabicyclo[2.2.2]oct-7-ene: tool for the stereoselective synthesis of polysubstituted piperidines. The Journal of organic chemistry. 2012 Jul 6;77(13):5832-7