Synthesis of nitrogen-containing molecules by zinc-catalyzed [4+2] cycloaddition and photoredox-catalyzed C-H functionalization
This work first describes an enantioselective Zn-catalyzed [4+2] cycloaddition of 1-azadienes and nitro-alkenes for the synthesis of medicinally valuable piperidines. The detrimental coordination of 1-azadienes to the Zn catalysts undermines the stereochemical control of the reaction. Fortunately, a novel bisoxazoline ligand limits this undesired coordination and delivers high stereoselectivity. Mechanistic studies suggest the reaction proceeds via a stepwise mechanism in which aza-Michael addition is followed by cyclization. This proposed mechanism also explains the successful cycloaddition ...