<i>N</i>-Alkoxy-4-methyl-5-(<i>p</i>-anisyl)thiazole-2(3<i>H</i>)thiones - New Precursors for Visible Light- or Thermally-Induced Alkoxyl Radical Reactions in Synthesis

Abstract

Visible light-initiated or thermally induced N-O homolysis of hitherto unknown 4-methyl-5-(p-anisyl)-substituted N-alkoxythiazolethiones furnishes alkoxyl radicals, which have been applied in the diastereoselective synthesis of bicyclic tetrahydro­furan rac-5 (5-exo-trig cyclization), formation of erythrose derivative 8 (β-C,C cleavage), and the preparation of bromoalcohol 10 (via selective 1,5-H-translocation), optionally under tin-free conditions.