Stereoselective synthesis of β-rhamnopyranosides via gold(<scp>i</scp>)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors

Abstract

Stereoselective β-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed SN2-like glycosylation protocol employing α-rhamnopyranosyl 2-alkynyl-4-nitro-benzoates as donors.