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Bromonitrile oxide formed in situ from dibromoformaldoxime reacts with the sugar derived alkenes 1, 2, 3, 4, to give bromoisoxazolines in satisfactory yields. All the reactions show high regio- and stereoselectivity. Reactions with the ω-unsaturated alkenes 1 and 2 are regiospecific and diastereoselective affording a pair of diastereomers. The reaction with furanone 4 is regioselective and stereospecific affording one pair of regioisomers, whereas the reaction with the glycal 3 is both regiospecific and stereospecific and gives only one isomer. The possible utility of the obtained isoxazolines as useful synthetic intermediates is further proved by transformation of isoxazoline 7 to 7-deoxy octose derivative 16.

Diastereoselective cycloaddition of bromonitrile oxide to sugar derived chiral alkenes. A possible route for the synthesis of higher deoxysugars