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.
Complete Stereoselective Synthesis of Quasienantiomeric Pseudo Imino-C-disaccharides: Parallel Kinetic Resolution of a Racemic cis-Dihydroxy Pyrroline N-oxide by 1,2-Glycals / F. Cardona; S. Valenza; A. Goti; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 1999:(1999), pp. 1319-1323.
Complete Stereoselective Synthesis of Quasienantiomeric Pseudo Imino-C-disaccharides: Parallel Kinetic Resolution of a Racemic cis-Dihydroxy Pyrroline N-oxide by 1,2-Glycals
CARDONA, FRANCESCA;VALENZA, SILVIA;GOTI, ANDREA;BRANDI, ALBERTO
1999
Abstract
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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