Cycloadditions of chiral pyrroline N-oxides to levoglucosenone (1) and isolevoglucosenone (2) proceed with a high level of double asymmetric induction. Partial kinetic resolutions (KR) of both enantiomers of a racemic nitrone 3 were achieved, and a parallel kinetic resolution (PKR) experiment allowed the stereoselective divergent synthesis of two quasienantiomeric imino-C-disaccharide precursors.