The major goal of this research program is to develop catalytic enantioselective transformations based on transition metal and chiral anion catalysis that will be broadly applicable to the preparation of therapeutically relevant organic molecules. Towards this end, new enantioselective reactions of carbon-carbon ?-bonds are proposed, with a major emphasis placed on the development of enantioselective sp3-C-F bond construction. Additionally, reactions that generate or employ available building blocks, such as alkenes and boronic acids, will be targeted. These methods will be exploited in the enantioselective construction of fluorinated building blocks, heterocycles and natural product analogs. Thus, we anticipate that the proposed air and moisture tolerant transformations will provide synthetic chemists and biomedical researchers with additional tools for molecular synthesis and for single enantiomer construction.
The proposed program aims to develop new methods for the preparation of structures and compounds of potential importance to medicinal chemistry. To this end, transition metal-catalyzed, organocatalytic and dual catalytic processes for synthesis of heterocyclic and carbocyclic structures, especially those containing carbon-fluorine bonds, are proposed.
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| Niemeyer, Zachary L; Pindi, Suresh; Khrakovsky, Dimitri A et al. (2017) Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization. J Am Chem Soc 139:12943-12946 |
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| Avila, Carolina M; Patel, Jigar S; Reddi, Yernaidu et al. (2017) Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts. Angew Chem Int Ed Engl 56:5806-5811 |
| Bohan, Patrick T; Toste, F Dean (2017) Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes. J Am Chem Soc 139:11016-11019 |
| Yang, Zhenyu; He, Ying; Toste, F Dean (2016) Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids. J Am Chem Soc 138:9775-8 |
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