Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2-cis-Selective Glycosylation

Dedication

This work is dedicated to Professor Hisashi Yamamoto on the occasion of his 82nd birthday.

Abstract

This account highlights an iron-catalyzed exclusively 1,2-cis-selective glycosylation method for aminoglycoside synthesis. This selective nitrogen atom transfer reaction is effective for a broad range of glycosyl donors and acceptors, and it can be operated in a reiterative fashion and scaled up to the multigram scale. Mechanistic studies revealed a unique yet generally applicable glycosylation mechanism in which the iron catalyst activates a glycosyl acceptor and an oxidant when it facilitates the cooperative atom transfer of both moieties to a glycosyl donor in an exclusively cis-selective manner.

Keywords

Stereoselective glycosylation - Nitrogen atom transfer - Iron catalysis - Aminoglycoside - Complex-carbohydrate synthesis

Publication History

Received: 02 June 2025

Accepted after revision: 14 July 2025

Accepted Manuscript online:
14 July 2025

Article published online:
20 August 2025

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