Enantioselective Hydroformylation with 3,4-Diazaphospholane Ligands

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Professor Clark R. Landis, Department of Chemistry, University of Wisconsin-Madison is supported by the Inorganic, Bioinorganic, and Organometallic Chemistry Program of the Chemistry Division to investigate the synthesis of new transition metal ligands and their applications in transition metal catalyzed reactions. One goal of this work is creation of new extensible and chiral 3,4-diazaphospholane ligands. Chiral 3,4-diazaphospholanes enable the synthesis of ligand libraries with diverse functional groups that create ?enzyme-like? environments around catalytically active transition metal centers. A second goal emphasizes application of 3,4-diazaphospholane-libraries to discover of catalysts for carbon-carbon bond forming reactions, such as hydroformylation, that yield chiral products with high selectivity and atom economy. Pharmaceutical intermediates constitute a major target. Understanding the mechanism by which 3,4-diazaphospholane ligands effect enantioselective hydroformylation of simple substrates such as styrene and vinyl acetate to produce chiral, functionalized aldehydes constitutes a third goal. Such mechanistic studies enable elucidation of the rate- and selectivity-determining reaction steps and how they are influenced by ligand structure.This project advances the state-of-the-art of enantioselective, transition-metal catalyzed transformations through the design and synthesis of novel organophosphine compounds. Efficient, selective, and atom economical transformations catalyzed by chiral transition metal complexes represent a critical technology for the synthesis of chiral pharmaceuticals, agrochemicals, and natural products. New enantioselective processes for hydroformylation resulting from this project will broadly impact organic synthesis by providing new pathways to chiral aldehydes and reducing waste associated with the production of enantiomerically pure stereogenic centers. This research provides graduate and undergraduate researchers with broad training and development of technical skills. The PI and students involved in this project will develop new hands-on activities to demonstrate the meaning and power of catalysis to novice chemistry students.