Synlett 2009(7): 1154-1156  
DOI: 10.1055/s-0028-1088105
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,3-Unsaturated O- and N-Glycosides by HBF4˙SiO2-Catalyzed Ferrier Rearrangement of d-Glycals

Oscar Mariano Rodríguez, Pedro Alfonso Colinas*, Rodolfo Daniel Bravo
LADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 y 115 (1900) La Plata, Argentina
Fax: +54(221)4226947; e-Mail: pcolinas@quimica.unlp.edu.ar;
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Received 1 January 2009
Publikationsdatum:
20. März 2009 (online)

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Abstract

Fluoroboronic acid adsorbed on silica gel (HBF4˙SiO2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.