A New Method to Generate α-Aminoalkyl Radicals: Treatment of Methyl α-Amino Selenoesters with Hydride Reagents. Synthesis of 6-Azabicyclo[3.2.1]octanes by Radical Cyclization

Article abstract of DOI:10.1055/s-1997-724

A new method to generate α-aminoalkyl radicals and its application to the synthesis of 6-azabicyclo[3.2.1]octanes is described. α-Amino selenoesters on heating with Bu₃SnH or (Me₃Si)₃SiH undergo decarbonylation of the initially formed acyl radical to give the corresponding α-amino radical which could be trapped intramolecularly with a double bond bearing an electron-withdrawing group.