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Synthesis 2000; 2000(7): 1027-1033
DOI: 10.1055/s-2000-6305
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Vitamin B12 Catalysis of Zinc-Mediated 6-Deoxy-6-iodopyranoside Fragmentation: A Mild and Convenient Preparation of ω-Unsaturated Hexose Derivatives (5-Hexenoses)

Martin Kleban* , Ulrich Kautz, Jörg Greul, Petra Hilgers, Rolf Kugler, Han-Qing Dong, Volker Jäger
  • *Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany; Fax +49(711)6854321; E-mail: jager.ioc@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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The known zinc-mediated preparation of 5-hexenoses by fragmentation of 6-iodopyranosides can be performed in a simple, fast, and mild way, with less side reactions, when vitamin B12 is employed as a catalyst.

fragmentation - zinc - vitamin B12 catalysis - 6-deoxy-6-iodopyranosides - 5-hexenoses