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A Stereoselective Route to Aza-C-aryl Glycosides from Arynes and Chiral Nitrones

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Title A Stereoselective Route to Aza-C-aryl Glycosides from Arynes and Chiral Nitrones
 
Creator KHANGAROT, RK
KALIAPPAN, KP
 
Subject Glycosides
Cycloaddition
Nitrogen heterocycles
Cyclic nitrones
Arynes
CYCLIC NITRONES
1,3-DIPOLAR CYCLOADDITION
RADICAMINE-B
NUCLEOPHILIC ADDITIONS
POLYHYDROXYLATED PYRROLIDINES
STRAIGHTFORWARD SYNTHESIS
DIPOLAR CYCLOADDITION
TERMINAL ALKYNES
NITRILE OXIDES
EN-ROUTE
 
Description 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.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-16T06:35:08Z
2014-10-16T06:35:08Z
2012
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (29)5844-5854
http://dx.doi.org/10.1002/ejoc.201200685
http://dspace.library.iitb.ac.in/jspui/handle/100/15447
 
Language en