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Paper | Special issue | Vol 79, No. 1, 2009, pp.883-896
Published online, 26th November, 2008
DOI: 10.3987/COM-08-S(D)59
N-Glycosylhydroxylamines as Masked Polyhydroxylated Chiral Nitrones in Cycloaddition Reactions: An Access to Pyrrolizidines

Marco Marradi, Massimo Corsi, Stefano Cicchi, Marco Bonanni, Francesca Cardona, and Andrea Goti*

*Department of Organic Chemistry “Ugo Schiff”, University of Florence, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy

Abstract

N-glycosylhydroxylamines undergo 1,3-dipolar cycloadditions via their tautomeric open chain nitrones. Cycloadditions to maleic acid esters occur with high diastereoselectivity and the products can be converted into highly functionalized pyrrolizidines.