[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines
We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in moderate to high yields. These resulting compounds can undergo subsequent transformations, demonstrating their utility as synthetic building blocks for more complex scaffolds. Finally, we propose a reasonable mechanism for this transformation using density functional theory modeling, justifying the experimental observations.
Hejnosz, S., Beres, D., Cocolas, A., Neal, M., Musiak, B., Hanna, M., Bloomfield, A., & Montgomery, T. (2023). [3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines. Organic Letters, 25 (25), 4638-4643. https://doi.org/10.1021/acs.orglett.3c01396