Stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as a gold(i)-catalyzed removable neighboring participation group

Abstract

In the present paper, we report a novel strategy for highly efficient stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as neighboring participation group. Subsequently, ortho-alkynyl benzoate can be removed smoothly in the presence of 5 mol% Ph₃PAuCl–AgOTf in dichloromethane with H₂O (1 eq.) and ethanol (6 eq.) to afford 2′-OH nucleosides in high yields and selectivity.