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Synlett 1992; 1992(3): 224-226
DOI: 10.1055/s-1992-21321
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Intramolecular Ritter-Like Reaction at the Anomeric Center of a Heptulose Derivative

Daan Noort* , Gijs A. van der Marel, Gerard J. Mulder, Jacques H. van Boom
  • *Gorlaeus Laboratories, Rijksuniversiteit Leiden, P.O. Box 9502, NL-2300 RA Leiden, The Netherlands
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Publication Date:
08 March 2002 (online)

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Treatment of 3,4,5,7-tetra-O-benzyl-α-D-gluco-2-heptulopyranose (1) with boron trifluoride-diethyl ether complex in acetonitrile or propionitrile results in the exclusive formation of the corresponding tetrahydropyran-2-spiro-4′-oxazolines 3,4, 11, and 12. Execution of the same reaction in trichloroacetonitrile yields a self-condensed dimer 10 as the sole product.