A Highly Enantioselective Copper/Phosphoramidite-Thioether-Catalyzed Diastereodivergent 1,3-Dipolar Cycloaddition of Azomethine Ylides and Nitroalkenes

In contrast to the plethora of catalytic systems that enable access to any enantiomers of the chiral products by simply choosing between a pair of enantiomeric or pseudoenantiomeric chiral catalysts, few analogously effective protocols exist for the synthesis of compounds bearing multiple stereogenic centers with full control of the absolute and relative stereochemical configurations. Here, we report the application of our previously developed modular phosphoramidite-thioether ligands for the copper-catalyzed diastereodivergent asymmetric 1,3-dipolar cycloaddition of azomethine ylides and nitroalkenes. Our catalytic system enables wide substrate scope, great stereochemical control, and high reaction efficiency.