Regio- and face-selective 1,3-dipolar cycloadditions to levoglucosenone

Abstract

Benzonitrile oxide and C,N-diphenylnitrone undergo highly regio- and face-selective cycloaddition reactions with levoglucosenone; in each case the major product results from approach anti to the 1,6-bridge of levoglucosenone, the oxygen of the 1,3-dipole becoming attached to the β-carbon of the enone unit.