ChemInform Abstract: 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.

✍ Scribed by J. QUIRANTE; C. ESCOLANO; J. BONJOCH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199727067

✦ Synopsis

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.

-α-Amino selenoesters on heating with Bu3SnH or Tms3SiH undergo decarbonylation to afford intermediate α-aminoalkyl radicals, which are trapped either intramolecularly to give bicycles (II) and ( III) or simply reduced to give amines (V) and (VII). The β-amino selenoester (VIII) reacts in a different way with hydride reagents. The homomorphan skeletons (IX) and (X) are formed as result of intramolecular addition of an acyl radical to the double bond. -(QUIRANTE,