Cycloadditions of hydroxylated enantiopure pyrroline N-oxides to 1,2-glycals display high double-asymmetric induction. The selectivity is controlled by the stereochemistry at C-3 of the glycal. A parallel kinetic resolution experiment with a racemic cis-dihydroxypyrroline N-oxide allowed the synthesis of two different pseudo imino-C-disaccharides precursors in a completely enantiopure form, totally avoiding the formation of minor cycloadducts.
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Cardona et al. (1999) studied this question.
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