A Synthetic Route to Functionalized Thiopyran Derivatives via Domino Ring-Opening Cyclization (DROC) of Donor–Acceptor Cyclopropanes with Pyridinium Thiolates
An efficient route to 5,6-dihydro-4<i>H</i>-thiopyran derivatives is developed via domino ring-opening cyclization (DROC) of activated donor-acceptor (DA)-cyclopropanes with pyridinium thiolates in the presence of Yb(OTf)<sub>3</sub> as the Lewis acid and K<sub>2</sub>CO<sub>3</sub> as the base under mild conditions in moderate to excellent yields. Enantiospecific S<sub>N</sub>2-type DROC of nonracemic DA-cyclopropane (ee 97%) with pyridinium thiolate afforded the corresponding nonracemic thiopyran product with high yield and excellent enantiospecificity (>97%). This approach offers a straightforward and practical route to thiopyran frameworks of synthetic and biological significance.
Authors
- Manas K. Ghorai (ORCID: https://orcid.org/0000-0002-0472-4757)
- Amit Kumar Sharma (ORCID: https://orcid.org/0000-0001-5255-5452)
- Poulami Mandal (ORCID: https://orcid.org/0000-0001-8903-7907)
- Partha Pratim Manna (ORCID: https://orcid.org/0000-0003-2939-0818)
- S. P. YADAV
Institutions
- Indian Institute of Technology Kanpur (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-13
- DOI
- https://doi.org/10.1021/acs.joc.5c00292
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Indian Institute of Technology Kanpur
- Department of Science and Technology, Ministry of Science and Technology, India
- University Grants Commission
- Science and Engineering Research Board