Intramolecular Ritter-Like Reaction at the Anomeric Center of a Heptulose Derivative

Abstract
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.

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