Versatility of Ketonitrones in the Synthesis of Key C-C and C-N Bonds in Biologically Relevant Molecules

Our group’s development of N-O and C-N bonds via Chan-Lam coupling between oximes and boronic acids positioned us to discover N-aryl and N-vinyl ketonitrones. N-aryl and N-vinyl ketonitrones with allenes or isocyanates as coupling partners are highly reactive starting materials and extremely sensitive to their reaction conditions. Controlling N-aryl and N-vinyl ketonitrones has been fruitful in the development of unique addition and rearrangement reactions to afford key C-C and C-N bonds in the formation of biologically relevant heterocycles such as 1,4-enaminoketones, amidines, and enantioenriched dihydropyridoindoles.