Enantioselective Reactions with Amide Electrophiles Utilizing Transition-Metal Catalysis

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Project Summary/Abstract Organic synthesis plays a crucial role in the development of small molecule therapeutics. New methodologies that allow for the introduction of defined stereocenters and difficult-to-access motifs, such as quarternary stereocenters, are particularly desirable. Moreover, there is growing interest in the use of unconventional synthetic building blocks to generate such complexity, as the use of uncommon starting materials provides new strategies and retrosynthetic disconnections that may prove broadly useful. The proposed research involves the use of amides in transition metal-catalyzed reactions to generate enantioenriched products bearing quaternary stereocenters. Although amides have historically been avoided as synthetic building blocks, they have recently been employed in transition metal-catalyzed reactions that proceed via C–N bond activation. However, amide cross-coupling methods that make quaternary stereocenters are rare and no catalytic enantioselective examples have been reported. The success of the proposed studies would push the limits of known amide cross- coupling methodology, provide methods to access defined quaternary stereocenters, and offer new strategies for synthetic chemists to utilize in the construction of drugs and complex molecules.