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Synlett 1997; 1997(2): 181-182
DOI: 10.1055/s-1997-727
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Generation of 1-Amidoalkyl Radicals from N-Protected Amino Acids: An Alternative to the Barton Decarboxylation Procedure

Aleksandar Stojanovic, Philippe Renaud*
  • *Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg (Switzerland) Fax: 41 26 300 87 77; E-mail: philippe.renaud@unifr.ch
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Publication Date:
31 December 2000 (online)

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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.

amino acids - selenoesters - radicals - decarbonylation - decarboxylation