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Synlett 1994; 1994(11): 916-918
DOI: 10.1055/s-1994-23047
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Medium Size Ether Ring Formation of C-Alkynylated Sugars via Dicobalthexacarbonyl Complexes

Minoru Isobe* , Chavi Yenjai, Shigeyoshi Tanaka
  • *Laboratory of Organic Chemistry, School of Agricultural Sciences, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
22 March 2002 (online)

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Four C-alkynylated compounds at the C-1 position of D-glucal were converted into the corresponding dicobalthexacarbonyl complexes, which recyclized upon treatment with acid to form the medium size (7, 8, 9 and 10 membered) rings. Decomplexation was difficult under the usual oxidative condition, but it successfully worked under reductive condition in the presence of rhodium catalyst under high pressure hydrogen atmosphere.