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

• Published in: Tetrahedron 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
• Language: English
• 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; ACCESS

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...