Dichotomous Selectivity in Indium-Mediated Aza-Barbier-Type Allylation of 2-N-Acetyl Glycosyl Sulfinylimines in Brine: Convenient Access to Potent Anti-Influenza Agents

Abstract

A highly diastereoselective indium-mediated allylation of 2-N-acetyl glycosyl sulfinylimines in brine under mild reaction conditions is reported. The method allows the achievement of a highly remarkable dichotomous selectivity for substrates, providing a single diastereoisomer of the product in 80–98% yield. With chiral (S)-homoallylic sulfinamide (R S)-5 and (R S)-8 formed as key intermediates, two potent anti-influenza agents, zanamivir and zanaphosphor, were synthesized in 50% and 41% overall yields, respectively.