Generation of 1-Amidoalkyl Radicals from N-Protected Amino Acids: An Alternative to the Barton Decarboxylation Procedure

Article abstract of DOI:10.1055/s-1997-727

An alternative method to the Barton decarboxylation procedure of N-protected amino acids is presented. The carboxylic acids are transformed into stable phenylselenoesters. Upon standard radical reaction conditions, they generate acyl radicals which undergo a very fast decarbonylation reaction to N-protected 1-aminoalkyl radicals. The decarbonylated radicals are trapped reductively and by intermolecular additions to olefins.