Grob fragmentation of 2-azabicyclo[2.2.2]oct-7-ene: tool for the stereoselective synthesis of polysubstituted piperidines.
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.
Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal QC H3C 3J7, Canada.
Gérald
G
Lemonnier
André B
AB
Charette
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
C576031:2-azabicyclo(2.2.2)oct-7-ene; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010880:Piperidines