Synlett 2003(2): 0227-0229
DOI: 10.1055/s-2003-36794
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Jens Hartung*, Thomas Gottwald, Kristina Špehar
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)8884606; e-Mail: hartung@chemie.uni-wuerzburg.de;
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Publication History

Received 24 October 2002
Publication Date:
22 January 2003 (online)

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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.