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

Yadav, J. S. ; Subba Reddy, B. V. ; Narasimha Chary, D. ; Madavi, C. ; Kunwar, A. C. (2009) First example of the carbon-Ferrier rearrangement of glycals with isocyanides: a novel synthesis of C-glycosyl amides Tetrahedron Letters, 50 (1). pp. 81-84. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.10.090

Abstract

Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl3 under mild reaction conditions to provide C-glycosyl amides in good yields with high α-selectivity. The use of FeCl3 makes this method simple, convenient and cost-effective. This is the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Ferrier Rearrangement; Glucal; Isocyanides; C-glycosyl Amides
ID Code:59606
Deposited On:07 Sep 2011 05:58
Last Modified:07 Sep 2011 05:58

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