[3 + 2] Cycloadditions of Tertiary Amine -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.

Multi-Ion Bridged Pathway of -Oxides to 1,3-Dipole Dilithium Oxide Complexes.

Roussi's landmark work on the generation of 1,3-dipoles from tertiary amine -oxides has not reached its full potential since its underlying mechanism is neither well explored nor understood. Two competing mechanisms were previously proposed to explain the transformation involving either an iminium ion or a diradical intermediate. Our investigation has revealed an alternative mechanistic pathway that explains experimental results and provides significant insights to guide the creation of new -oxide reagents beyond tertiary alkylamines for direct synthetic transformations.