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Note | Regular issue | Vol 68, No. 12, 2006, pp.2607-2613
Published online, 24th October, 2006
DOI: 10.3987/COM-06-10812
Exclusive Formation of α-Anomers in NbCl5-Promoted Ferrier Rearrangement for the Synthesis of 2,3-Unsaturated Glycosides

Ronaldo N. de Oliveira, Adriana C. N. de Melo, Rajendra M. Srivastava,* and Denis Sinou

*Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50740-540, Recife, PE, Brazil

Abstract

NbCl5-catalyzed reaction of primary and secondary alcohols with tri-O-acetyl-D-glucal is described. Exclusive formation of α-anomers of eight 2,3-unsaturated glycosides (3a-h) in high yields has been observed. Among eight unsaturated glycosides (3a-h) prepared, two of them (3d,e) are new. A new mechanism of the formation of (3a-h) from tri-O-acetyl-D-glucal and an alcohol assisted by NbCl5 as a catalyst has been suggested.