Intramolecular 1,3-dipolar cycloaddition of N-alkenyl nitrones en route to glycosyl piperidines

Stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral N-(alkenylglycosyl)nitrones, prepared by allylation of C-(glycosyl)nitrones and subsequent oxidation, is described. The previously described 2-aza-Cope rearrangement was not observed for these substrates, but evidences of E/ Z is...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 51; pp. 7152 - 7155
Main Authors Marca, Eduardo, Delso, Ignacio, Tejero, Tomás, Vázquez, Jesús T., Dorta, Rosa L., Merino, Pedro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.12.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Iminodisaccharides
Intramolecular dipolar cycloaddition
Nitrones
Physical Sciences
Piperidines
Science & Technology
Nitrones
Intramolecular dipolar cycloaddition
Piperidines
Iminodisaccharides
AZA-C-DISACCHARIDES
ALLYLATION
AGLYCON
ADDITIONS
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Summary:Stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral N-(alkenylglycosyl)nitrones, prepared by allylation of C-(glycosyl)nitrones and subsequent oxidation, is described. The previously described 2-aza-Cope rearrangement was not observed for these substrates, but evidences of E/ Z isomerism during the cycloaddition were obtained. The obtained cycloadducts can serve as key precursors of imino disaccharide analogues. This is exemplified by a short route to a protected 2-furanosyl-4-hydroxy-6-phenyl piperidine.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.10.023