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Synthesis of a Ligand for Enantioselective Catalysis

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Many chemical reactions yield enantiomer products, which are compounds that have the same type and number of bonds but are non-superimposable mirror images of each other, similar to one’s right and left hands. The enantiomers’ different spatial arrangements make them react differently with other enantiomer compounds. For example, enzymes in our bodies are chiral (single enantiomers), so they interact with each of the enantiomer forms of another chiral molecule differently. If a drug is administered as a racemic mixture (a 50:50 mixture of its enantiomer forms), each enantiomer can be metabolized differently; one producing the desired effect while the other may produce severe undesired side effects. Enantioselective catalysis is one method for controlling which enantiomer is produced. Our focus is on preparing organic molecules (ligands) that can be used with a metal to form catalysts; the catalysts will be used for numerous reactions to determine its effectiveness in driving the reaction to form only one enantiomer form. Our ligand is prepared in a 2-step process; an in-situ cadmium-bound ligand complex formation followed by isolating the ligand from the complex using a thiol-based substitution reaction. The isolated ligand can then be bound to a metal to form a potential enantioselective catalyst. The work on the isolation of the ligand will be presented, along with the progress on developing new metal-ligand complexes for use as potential enantioselective catalysts.

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Synthesis of a Ligand for Enantioselective Catalysis

Many chemical reactions yield enantiomer products, which are compounds that have the same type and number of bonds but are non-superimposable mirror images of each other, similar to one’s right and left hands. The enantiomers’ different spatial arrangements make them react differently with other enantiomer compounds. For example, enzymes in our bodies are chiral (single enantiomers), so they interact with each of the enantiomer forms of another chiral molecule differently. If a drug is administered as a racemic mixture (a 50:50 mixture of its enantiomer forms), each enantiomer can be metabolized differently; one producing the desired effect while the other may produce severe undesired side effects. Enantioselective catalysis is one method for controlling which enantiomer is produced. Our focus is on preparing organic molecules (ligands) that can be used with a metal to form catalysts; the catalysts will be used for numerous reactions to determine its effectiveness in driving the reaction to form only one enantiomer form. Our ligand is prepared in a 2-step process; an in-situ cadmium-bound ligand complex formation followed by isolating the ligand from the complex using a thiol-based substitution reaction. The isolated ligand can then be bound to a metal to form a potential enantioselective catalyst. The work on the isolation of the ligand will be presented, along with the progress on developing new metal-ligand complexes for use as potential enantioselective catalysts.