In most synthetic systems, expensive and toxic transition-metal catalysts are often used to access chiral products with unique medicinal or material characteristics. In contrast, asymmetric organocatalysts modeled after naturally-occurring amino acids provide a similar catalytic ability, but with reduced toxicity and cost. These non-natural amino acids are especially of interest due to their unique stereochemistry and modifiability, which allow their catalytic ability to be carefully tuned for efficient asymmetric induction.<br/>As such, we are interested in non-natural amino acid derivatives containing sites for hydrogen bonding and enamine formation, allowing application in the catalysis of Michael additions between aldehydes and nitroalkenes. To approach this target molecule, a novel tandem conjugate addition, diazo transfer and 1,3-dipolar cycloaddition was employed to form a unique chiral non-natural amino acid scaffold. Subsequent reductive amination and isothiocyanation was then attempted. However, further optimization necessitated a reduction pathway to obtain the organocatalyst.

Synthesis of a chiral organocatalyst via a novel asymmetric tandem conjugate addition, diazo transfer and 1,3-dipolar cycloaddition

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.