A stereoselective route to aza-C-aryl glycosides from arynes and chiral nitrones

Khangarot, Rama Kanwar ; Kaliappan, Krishna P. (2012) A stereoselective route to aza-C-aryl glycosides from arynes and chiral nitrones European Journal of Organic Chemistry, 2012 (29). pp. 5844-5854. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.201200685

Abstract

Arynes are regarded as potential and versatile intermediates in organic synthesis. These highly-reactive, strained and kinetically unstable species have numerous applications in synthetic chemistry. In this article, a highly-diasteroselective and efficient 1,3-dipolar cycloaddition reaction between a range of arynes and sugar-derived cyclic nitrones leading to an interesting class of sugar-based benzo[d]isoxazolines is described. These benzo[d]isoxazolines upon selective N–O bond cleavage provide various substituted aza-C-aryl glycosides in good yield. These substituted pyrrolidine derivatives are chiral aminophenols and could be potential chiral ligands and organocatalysts in asymmetric synthesis.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons Inc.
Keywords:Glycosides; Cycloaddition; Nitrogen Heterocycles; Cyclic Nitrones; Arynes
ID Code:105007
Deposited On:19 May 2017 09:16
Last Modified:19 May 2017 09:16

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