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Synthesis of Saturated Heterocycles Via Enantioselective Copper-Catalyzed Polar-Radical Reactions of Alkenols and Alkenyl Amine Derivatives

March 22, 2022 - 11:00am to 12:00pm

Saturated oxygen and nitrogen heterocycles, e.g. pyrrolidines, morpholines and tetrahydrofurans, are prevalent in bioactive small molecules. The development of enantioselective cyclizations of alkenols and alkenylamine derivatives catalyzed by copper salts complexed to chiral ligands will be presented. The alkene additions are thought to occur via polar oxycupration and aminocupration. Subsequent bond-forming steps proceed via carbon radical intermediates and involve atom transfers, additions to p-bonds and organometallic processes. A family of alkene addition reactions has been developed and includes carboamination, carboetherification, hydroetherification, diamination, aminooxygenation and dioxygenation.  The latest additions to this reaction family will be disclosed. Efficient aspects include enantioselectivity, use of earth abundant copper as catalyst and application of aerobic conditions as oxidant and reagent. Applications to bioactive small molecule targets are included.

Location and Address

Zoom via following link: https://pitt.zoom.us/j/99563318495

Speakers

Professor Sherry Chemler - State University of New York at Buffalo