Tethered aza-Wacker cyclization reactions with unusual N-alkoxy carbamates
Substrates with <i>N</i>-alkoxy carbamate "heads" and olefin "tails" can be productively cyclized into 1,3-oxazinan-2-one products bearing pendant alkenes. Our reaction protocol is operationally simple and involves heating the substrate with a mixture of Pd (II) and Cu (II) salts in CH<sub>3</sub>CN under 1 atm of O<sub>2</sub>. We hypothesize that an <i>aza</i>-Wacker mechanism is operative, based on prior art and our own experience with this reaction class. An array of substrates is compatible, and the heterocyclic products are amenable to further transformations.
Authors
- Appasaheb K. Nirpal
- Dnyaneshwar A. Gorve
- Shyam Sathyamoorthi (ORCID: https://orcid.org/0000-0003-4705-7349)
- Steven P. Kelley (ORCID: https://orcid.org/0000-0001-6755-4495)
- R. H. Silver (ORCID: https://orcid.org/0009-0002-2661-7693)
Institutions
- University of Kansas (US)
- University of Missouri (US)
Publication Details
- Journal
- Tetrahedron
- Published
- 2025-05-17
- DOI
- https://doi.org/10.1016/j.tet.2025.134730
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Foundation for the National Institutes of Health
- National Institutes of Health