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Communication | Regular issue | Vol 65, No. 6, 2005, pp.1289-1294
Published online, 15th April, 2005
DOI: 10.3987/COM-05-10389
Double Diastereoselective Synthesis of syn,syn-Bis(1,2-isoxazolin-5-yl)methanol and syn,syn,syn-1,2-Bis(1,2-isoxazol-5-yl)ethane-1,2-diols: Facile Route for the Synthesis of Polyols

Bum Suk Son, Bo Gan Song, Jung Ki Kim, Min Jung Seo, Zaesung No, and Hyoung Rae Kim*

*Medicinal Science Division, Korea Research Institute of Chemical Technology, P. O. Box 107, Yusong, Taejon 305-600, Korea

Abstract

syn,syn-Bis(1,2-isoxazolin-5-yl)methanols and syn,syn,syn-1,2-bis(1,2-isoxazol-5-yl)ethane-1,2-diols were synthesized from various nitrile oxides with 1,4-pentadien-3-ol and 1,5-hexadiene-3,4-diol respectively in the presence of ethylmagnesium bromide by double diastereoselective 1,3-dipolar cycloaddition reaction. The resulting isoxazolines were converted to the corresponding new polyols by hydrogenolysis with Raney Ni.