Iron-Catalyzed Aerobic Hydration of Glycal: A Route toward Deoxy Sugars/Glycosides

We report an iron-catalyzed protocol for the efficient functionalization of glycals. Employing inexpensive iron(III) or iron(II) chloride as a catalyst and phenylsilane (PhSiH<sub>3</sub>) as an additive, this method enables the high-yield synthesis of 2-deoxy sugars and glycosides. A key modification of the Mukaiyama hydration reaction, this approach directly utilizes air as the oxygen source. It demonstrates robust activity across both protected and unprotected glycals, with notably excellent yields observed for ester-protected substrates. Its utility is further highlighted through coupling reactions with bioactive molecules, affording diverse 2-deoxy sugar derivatives.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-10
DOI
https://doi.org/10.1021/acs.joc.5c01820
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
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article

Iron-Catalyzed Aerobic Hydration of Glycal: A Route toward Deoxy Sugars/Glycosides

Zongquan Wang, Yang Qi-chang, Jian Lyu, Haifeng Wang et al.
The Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
article

Iron-Catalyzed Aerobic Hydration of Glycal: A Route toward Deoxy Sugars/Glycosides

Zongquan Wang, Yang Qi-chang, Jian Lyu, Haifeng Wang, Shuang‐Xi Gu, Qiang Zhang, Jian Yao
article en

Abstract

We report an iron-catalyzed protocol for the efficient functionalization of glycals. Employing inexpensive iron(III) or iron(II) chloride as a catalyst and phenylsilane (PhSiH<sub>3</sub>) as an additive, this method enables the high-yield synthesis of 2-deoxy sugars and glycosides. A key modification of the Mukaiyama hydration reaction, this approach directly utilizes air as the oxygen source. It demonstrates robust activity across both protected and unprotected glycals, with notably excellent yields observed for ester-protected substrates. Its utility is further highlighted through coupling reactions with bioactive molecules, affording diverse 2-deoxy sugar derivatives.

The Journal of Organic ChemistryVol. 90(46)
Hubei University of Education (CN), Florida Cancer Care (US), Wuhan Institute of Technology (CN)
Openalex Percentile: Top 75%
Carbohydrate Chemistry and Synthesis
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