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Synlett 2001; 2001(10): 1620-1622
DOI: 10.1055/s-2001-17476
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Reductive Ring Opening of 6-Deoxy-6-iodopyranosides and 5-Deoxy-5-iodofuranosides by Manganese. A Convenient Procedure for the Preparation of Chiral 5-Hexenals and 4-Pentenals

Kazuho Tanaka* , Shinjiro Yamano, Oyo Mitsunobu
  • *Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University, Chitosedai, Setagayaku, Tokyo 157-8572, Japan; E-mail: mitsu@chem.aoyama.ac.jp
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Publication History

Publication Date:
27 September 2001 (online)

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Reaction of fully protected 6-iodopyranosides and 5-iodofuranosides with Mn in the presence of trimethylsilyl chloride and PbCl2 (Takai-conditions) afforded the corresponding 5-hexenals and 4-pentenals in good to moderate yields.

reductive sugar-ring opening - manganese - chiral 5-hexenals - chiral 4-pentenals