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Synlett 2001; 2001(6): 0749-0752
DOI: 10.1055/s-2001-14598
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Cyclopentyl and Carbohydrate Derivatives of N-Hydroxy-4-methylthiazole-2(3H)-thione: Synthesis by Mitsunobu Reaction and Highly Selective Photochemical Conversion into Aldehydes

Jens Hartung* , Thomas Gottwald, Rainer Kneuer
  • *Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany; Fax + 49 (0)931/888 4606; E-mail: hartung@chemie.uni-wuerzburg.de
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Publication Date:
31 December 2001 (online)

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Substituted N-cyclopentoxy- and carbohydrate-derived thiazole-2(3H)-thiones 3 were prepared from alcohols 2 or from 2,3:5,6-di-O-isopropylidene mannose in the presence of PPh3, diethyl azodicarboxylate (DEAD), and N-hydroxy-4-methylthiazole-2(3H)-thione (1). Alkoxy radical precursors 3 were photoreacted with hydrogen atom donors to afford substituted aldehydes 7 or formyl esters 10-11 via highly regioselective alkoxy radical fragmentations.

alkoxy radical - carbohydrate - β-cleavage - Mitsunobu reaction - thiazolethione

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