Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 29, Pages 5844-5854Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200685
Keywords
Glycosides; Cycloaddition; Nitrogen heterocycles; Cyclic nitrones; Arynes
Categories
Funding
- Department of Science and Technology (DST), New Delhi
- DST
- AstraZeneca Research Foundation
- Council of Scientific and Industrial Research (CSIR), New Delhi
Ask authors/readers for more resources
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 NO 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available