Intramolecular 1,3-dipolar cycloaddition of N-alkenyl nitrones en route to glycosyl piperidines |
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| Authors: | Eduardo Marca,Tomá s Tejero,Rosa L. Dorta |
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| Affiliation: | a Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragon, Universidad de Zaragoza, CSIC, E-50009 Zaragoza, Aragon, Spain
b Instituto Universitario de Bio-Orgánica ‘Antonio González’, Departamento de Química Orgánica, Universidad de La Laguna, E-38206 La Laguna, Tenerife, Spain |
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| Abstract: | 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. |
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| Keywords: | Nitrones Intramolecular dipolar cycloaddition Piperidines Iminodisaccharides |
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