Chemo-, Regio-, and Stereoselective Carbon-Carbon Bond Forming Processes using Innovative Alkene Oxidative Coupling Strategies

Principal Investigator

Masafumi HIRANO (Professor, Tokyo University of Agriculture and Technology)

Outline of the Project

In the present study, we develop linear cross dimerization of substituted alkenes.  In particular, our novel catalyst chemoselectively binds coordinatively to two different alkenes through their prosetereogenic faces, and then forms a metallacyclopentane by an oxidative coupling mechanism.  Afterward, the successive rapid migration of a hydrogen atom in the metallacyclopenane releases an enantioselective linear cross dimer as a product.  The present carbon-carbon bond forming reaction shows 100% atom efficiency and never generates waste from the reaction itself.  This new methodology provides us new synthetic pathways for biologically active agents, amino acids, and pharmaceutical intermediates.


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