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

Abstract

AbstractArynes 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.