Metal-Catalyzed Asymmetric Arylation of Silyloxy Dienes

Massachusetts Institute Of Technology, Cambridge MA

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Abstract

DESCRIPTION (provided by applicant): Optically pure gamma-aryl lactones and gamma-aryl lactams are general structural subunits in many biologically active natural products and pharmacologically important molecules. They have also found use as important intermediates for the synthesis of natural products. Access to these types of compounds has been limited. A transition metal (Pd, Ni, Cu) catalyzed asymmetric arylation of furan- and pyrrole based silyloxy dienes is proposed to gain access to this type of compound. Various factors influencing the proposed process including co-catalyst will be examined to better understand the transition metal catalyzed arylation processes. An interesting asymmetric Patesis-Ferrier type rearrangement is proposed. This will provide access to asymmetric quaternary centers under mild acidic conditions. The application of the proposed methodology in the synthesis of natural products is proposed. The potential targets include natural and unnatural amino acids, erythrina alkaloids and other synthetically important subunits.