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Synlett 1997; 1997(2): 179-180
DOI: 10.1055/s-1997-724
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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

Josefina Quirante, Carmen Escolano, Josep Bonjoch*
  • *Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain, Fax 34.3.4021894; E-mail bonjoch@farmacia.far.ub.es
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Publication Date:
31 December 2000 (online)

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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.

radical cyclization - α-aminoalkyl radical - α-amino selenoesters - decarboxylation - bridged azabicyclic compounds