π-Facial Selectivity in the Cycloaddition of Nitrile Oxides to 5,6-Dideoxy-5-Enofuranoses |
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| Authors: | Alexander J Blake Graeme Kirkpatrick Karen E McGhie R Michael Paton Kenneth J Penman |
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| Institution: | Department of Chemistry , The University of Edinburgh , West Mains Road, Edinburgh, EH9 3JJ, UK |
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| Abstract: | Abstract Benzonitrile oxide and ethoxycarbonylformonitrile oxide cycloadd regiospecifically and diastereoselectively to α-methyl 5,6-dideoxy-2,3-O-isopropylidene-d-lyxo-hex-5-enofuranoside 7 to afford isoxazolines 10 and 11. The π-facial selectivity (ca. 7:1) is comparable with that observed for xylo-alkene 1, and much greater than that for its ribo-isomer 4. The structure of isoxazoline 10a was determined by X-ray crystallography. |
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