Nitrone cycloadditions to isolevoglucosenone: ready access to a new class of directly linked (1-->3)-imino-C-disaccharides

Francesca Cardona; Andrea Goti; Alberto Brandi

doi:10.1021/ol0342507

Nitrone cycloadditions to isolevoglucosenone: ready access to a new class of directly linked (1-->3)-imino-C-disaccharides

Org Lett. 2003 May 1;5(9):1475-8. doi: 10.1021/ol0342507.

Authors

Francesca Cardona¹, Andrea Goti, Alberto Brandi

Affiliation

¹ 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

PMID: 12713302
DOI: 10.1021/ol0342507

Abstract

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]

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic
Carbohydrate Conformation
Cyclization
Disaccharides / chemical synthesis*
Disaccharides / chemistry*
Nitrogen Oxides / chemistry*
Pyrroles / chemistry
Stereoisomerism

Substances

1,6-anhydro-2,3-dideoxyhex-3-enopyran-4-ulose
Bridged Bicyclo Compounds, Heterocyclic
Disaccharides
Nitrogen Oxides
Pyrroles
nitrones