Thursday, November 21, 2024
11/21/2024
Project Summary/Abstract Chiral amino functionalized molecules are common motifs in a variety of bioactive molecules. They are also important chiral building blocks in organic synthesis such as the chiral ligand frameworks that are the pillars in several fields of asymmetric catalysis. The functional importance of these molecules renders their synthesis continuously in high demand. Catalytic processes that can directly utilize abundant chemical feedstocks to achieve the synthesis of these functional molecules are ideal. However, significant challenges remain for the development of such catalytic reactions. The main objective of this program is to develop new classes of catalytic and asymmetric alkene difunctionalizations and other processes that will meet the demands of these challenges and expedite access to chiral amino functionalized motifs. Specifically, this proposal will introduce chiral hypervalent iodine and halonium catalysis as platforms to resolve the regiochemical and enantioselective challenges often encountered in these reactions. Our preliminary data and proposed studies will enable us to: 1) utilize chiral hypervalent iodine catalysis to achieve asymmetric induction for practical olefin oxyamination and explore this class of catalysts as a new element for regiochemical control; and 2) initiate the use of a non- covalent interaction (NCI) – halogen bonding for catalysis development and chemical reaction engineering. Our proposal is innovative based on common and classic intermediates that are comprehensive to undergraduate students to introduce several means of new strategies for regiochemical control and engage an uncommon NCI for catalysis development. These methods use only simple and ubiquitous bifunctional reagents such as amide, urea, carbamate, alcohols, etc as the functionalization reagents. Importantly, our strategy will enable a straightforward route for the asymmetric synthesis of chiral amino functionalized motifs.
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