The invention of radical reactions. Part XXXVIII. Homologation of carboxylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer

Article abstract of DOI:10.1016/S0040-4020(97)00543-7

Alkyl radicals generated from O-acyl derivatives of N-hydroxy-2-thiopyridone added onto acrylamide at room temperature to form crystalline 2-(2-pyridylsulfanyl)-carbosamides. Desulfurization of the latter by nickel boride at roam temperature afforded primary amides in quantitative yield. 3-Deoxy-D-arabino-2-heptulosonic acid (DAH), its 4-epimer, and their derivatives were effectively synthesized from commercial D-ribonolactone by similar radical chemistry.