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.
Authors
- Zongquan Wang
- Yang Qi-chang
- Jian Lyu (ORCID: https://orcid.org/0009-0006-0036-3735)
- Haifeng Wang (ORCID: https://orcid.org/0000-0003-2277-4528)
- Shuang‐Xi Gu (ORCID: https://orcid.org/0000-0003-0159-4616)
- Qiang Zhang (ORCID: https://orcid.org/0000-0003-2787-1781)
- Jian Yao (ORCID: https://orcid.org/0000-0002-4716-5270)
Institutions
- Hubei University of Education (CN)
- Florida Cancer Care (US)
- Wuhan Institute of Technology (CN)
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
- 0.00