The major goal of this research program is to develop catalytic enantioselective transformationsbasedontransitionmetalandchiralanioncatalysisthatwillbebroadly applicabletothepreparationoftherapeuticallyrelevantorganicmolecules.Towardsthis 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 theenantioselectiveconstructionoffluorinatedbuildingblocks,heterocyclesandnatural product analogs. Thus, we anticipate that the proposed air and moisture tolerant transformations will provide synthetic chemists and biomedical researchers with additionaltoolsformolecularsynthesisandforsingleenantiomerconstruction.
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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| Zhukhovitskiy, Aleksandr V; Kobylianskii, Ilia J; Wu, Chung-Yeh et al. (2018) Migratory Insertion of Carbenes into Au(III)-C Bonds. J Am Chem Soc 140:466-474 |
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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 |
| Levin, Mark D; Chen, Tiffany Q; Neubig, Megan E et al. (2017) A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation. Science 356:1272-1276 |
| 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 |
| Christian, Alec H; Niemeyer, Zachary L; Sigman, Matthew S et al. (2017) Uncovering Subtle Ligand Effects of Phosphines Using Gold(I) Catalysis. ACS Catal 7:3973-3978 |
| 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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