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

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.