Iron-Catalyzed Glycal cis -Aminoacyloxylation for 2-Amino Saccharide Synthesis

Le Yin; Dakang Zhang; Zixiang Jiang; Pinzhi Wang; Joseph C Levine; Dylan L Labbe; Hao Xu

doi:10.1016/j.tetlet.2025.155678

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Iron-Catalyzed Glycal cis -Aminoacyloxylation for 2-Amino Saccharide Synthesis

Journal article

Peer reviewed

Iron-Catalyzed Glycal cis -Aminoacyloxylation for 2-Amino Saccharide Synthesis

Le Yin, Dakang Zhang, Zixiang Jiang, Pinzhi Wang, Joseph C Levine, Dylan L Labbe and Hao Xu

Tetrahedron letters, Vol.167, 155678

08/30/2025

DOI: https://doi.org/10.1016/j.tetlet.2025.155678

PMID: 40487289

Abstract

1,2-cis-Aminoglycoside

Iron catalysis

Nitrogen atom transfer

Stereoselective glycosylation

We report here a new catalytic and exclusively 1,2- -selective glycal aminoacyloxylation method for 2-amino saccharide synthesis. This iron-catalyzed glycosylation is effective for a wide variety of glycosyl donors with consistently high stereoselectivity and excellent functional-group compatibility, which facilitates late-stage amino group incorporation for complex-carbohydrate synthesis.

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Title: Iron-Catalyzed Glycal cis -Aminoacyloxylation for 2-Amino Saccharide Synthesis
Creators: Le Yin - Brandeis University
Dakang Zhang - Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States
Zixiang Jiang - Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States
Pinzhi Wang - Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States
Joseph C Levine - Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States
Dylan L Labbe - Department of Chemistry, Brandeis University, 415 South Street, Waltham, Massachusetts 02453, United States
Hao Xu - Brandeis University
Publication Details: Tetrahedron letters, Vol.167, 155678
Grant note: R35 GM134926 / NIGMS NIH HHS S10 OD034395 / NIH HHS
Identifiers: 9924484865301921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Iron-Catalyzed Glycal cis -Aminoacyloxylation for 2-Amino Saccharide Synthesis

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