Development of iridium catalyzed enantioselective C-C bond coupling reactions



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Developing new methods to construct enantiomerically enriched higher alcohols via direct C-C bond formation is still a challenge worth pursing in modern synthetic organic chemistry. Enantiomerically enriched alcohols are important due to the abundance of these motifs found in polyketide natural products, a class of molecules widely explored for their bioactive properties. This thesis focuses on the development of iridium catalyzed reductive coupling reactions of allylic acetates with ethanol and symmetric ketones. Chapter 1 describes the utilization of ethanol, the world’s most abundant renewable C-2 feedstock, and its first use as coupling partner in the enantioselective synthesis of higher secondary alcohols. Chapter 2 explains the first systematic study of utilizing symmetric ketones as coupling partners in the synthesis of α-stereogenic tertiary alcohols. Demonstration of the use of these methodologies for the synthesis of pharmacologically inspired molecules is shown through the functional group tolerance of all the top 10 N-heterocycles most commonly found in FDA approve drugs.



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