Work

Tethered aza-Wacker cyclization reactions with unusual N-alkoxy carbamates

Year: 2025

Type: article

Abstract: ABSTRACT Substrates with N -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 3 CN under 1 atm of O 2 . We hypothesize that an aza -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.

Source: Tetrahedron

DOI: 10.1016/j.tet.2025.134730

Authors: Appasaheb K. Nirpal, Dnyaneshwar A. Gorve, Raju Silver, Steven P. Kelley, Shyam Sathyamoorthi

Institutions: University of Kansas, University of Missouri

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,680

Funders: Foundation for the National Institutes of Health, National Institutes of Health, National Institute of General Medical Sciences