First example of the carbon-Ferrier rearrangement of glycals with isocyanides: a novel synthesis of C-glycosyl amides

Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl 3 under mild reaction conditions to provide C-glycosyl amides in good yields with high α-selectivity. The use of FeCl 3 makes this method simple, convenient and cost-effective. This is...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 1; pp. 81 - 84
Main Authors Yadav, J.S., Reddy, B.V. Subba, Narasimha Chary, D., Madavi, C., Kunwar, A.C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.01.2009
Elsevier
Subjects
C-Glycosyl amides
Chemistry
Chemistry, Organic
Ferrier rearrangement
Glucal
Isocyanides
Physical Sciences
Science & Technology
Ferrier rearrangement
Isocyanides
C-Glycosyl amides
Glucal
GLUCALS
GLYCOPYRANOSIDES
ACIDS
TRIMETHYLSILYL CYANIDE
GLYCOSIDATION
SILYLACETYLENES
STEREOSELECTIVE SYNTHESIS
Online AccessGet full text

Cover

More Information
Summary:Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl 3 under mild reaction conditions to provide C-glycosyl amides in good yields with high α-selectivity. The use of FeCl 3 makes this method simple, convenient and cost-effective. This is the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.10.090