Complete stereoselective synthesis of quasi-enantiomeric pseudo imino-C-disaccharides: Parallel kinetic resolution of a racemic cis-dihydroxypyrroline N-oxide by 1,2-glycals

Authors
Cardona, F Valenza, S Goti, A Brandi, A
Citation
F. Cardona et al., Complete stereoselective synthesis of quasi-enantiomeric pseudo imino-C-disaccharides: Parallel kinetic resolution of a racemic cis-dihydroxypyrroline N-oxide by 1,2-glycals, EUR J ORG C, (6), 1999, pp. 1319-1323
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
6
Year of publication
1999
Pages
1319 - 1323
Database
ISI
SICI code
1434-193X(199906):6<1319:CSSOQP>2.0.ZU;2-7
Abstract
Cycloadditions of hydroxylated enantiopure pyrroline N-oxides to 1,2-glycal s display high double-asymmetric induction. The selectivity is controlled b y the stereochemistry at C-3 of the glycal. A parallel kinetic resolution e xperiment with a racemic cis-dihydroxypyrroline N-oxide allowed the synthes is of two different pseudo imino-C-disaccharides precursors in a completely enantiopure form, totally avoiding the formation of minor cycloadducts.