Nitrone cycloadditions to isolevoglucosenone: ready access to a new class of directly linked (1-->3)-imino-C-disaccharides.
Straightforward access to a new class of d-gulo- and d-allo-derived directly linked (1-->3)-imino-C-disaccharides by means of cycloaddition reactions of enantiopure polyhydroxylated pyrroline N-oxides with isolevoglucosenone is reported. The cycloaddition reactions display a high level of double asymmetric induction, which allows a partial kinetic resolution of a racemic nitrone. [reaction: see text]
Cardona
Francesca
F
Dipartimento di Chimica Organica Ugo Schiff, Polo Scientifico, Università di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino, Florence, Italy. francesca.cardona@unifi.it
Goti
Andrea
A
Brandi
Alberto
A
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002236:Carbohydrate Conformation; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
C476164:1,6-anhydro-2,3-dideoxyhex-3-enopyran-4-ulose; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004187:Disaccharides; D009589:Nitrogen Oxides; D011758:Pyrroles; C015388:nitrones