Tandem Organocatalysis: Chlorination-Michael-Aldol Reaction

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DESCRIPTION (provided by applicant): Transforming simple achiral molecules into stereochemically complex molecules remains a central challenge in organic synthesis. Asymmetric metal catalysis provides an avenue to meet this challenge. However, the majority of asymmetric organometallic catalysts mediates one type of reaction and allows one transformation. Therefore, traditionally complex organic molecules are often built transformation by transformation. This process is tedious and expensive. This proposal describes an innovative approach to asymmetric catalysis, asymmetric tandem organocatalysis, which uses one catalyst to mediate multiple transformations. The utility of tandem organocatalysis will be demonstrated in a very concise synthesis of Eiseniachloride A, a molecule of potential great medicinal interest. The completion of this proposed research would show the concept of tandem organocatalysis is valid and superior to the traditional one catalyst-one transformation organometallic catalysis. More importantly, the realization of asymmetric tandem organocatalysis would provide large quantities of potential drug candidates that can not be obtained otherwise.