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A Stereoselective Route to Aza‐ C ‐aryl Glycosides from Arynes and Chiral Nitrones
Author(s) -
Khangarot Rama Kanwar,
Kaliappan Krishna P.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200685
Subject(s) - chemistry , cycloaddition , aryne , aryl , stereoselectivity , bond cleavage , combinatorial chemistry , reactive intermediate , stereochemistry , organic chemistry , catalysis , alkyl
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.