http://repository.iitr.ac.in/handle/123456789/3052| Title: | Direct Enantio-and Diastereoselective Zn-ProPhenol-Catalyzed Mannich Reactions of CF3-and SCF3-Substituted Ketones |
| Authors: | Trost B.M. Hung C.-I.J. Mata G. Liu Y. Lu Y. Gnanamani, Elumalai |
| Published in: | Organic Letters |
| Abstract: | Enantioselective incorporation of trifluoromethyl (-CF3) and trifuoromethylthio (-SCF3) groups in small molecules is of high interest to modulate the potency and pharmacological properties of drug candidates. Herein, we report a Zn-ProPhenol catalyzed diastereo-and enantioselective Mannich addition of ?-trifluoromethyl-and ?-trifuoromethylthio-substituted ketones. This transformation uses cyclic and acyclic ketones and generates quaternary trifluoromethyl and tetrasubstituted trifuoromethylthio stereogenic centers in excellent yields and selectivities. © 2020 American Chemical Society. |
| Citation: | Organic Letters (2020), 22(6): 2437-2441 |
| URI: | https://doi.org/10.1021/acs.orglett.0c00646 http://repository.iitr.ac.in/handle/123456789/3052 |
| Issue Date: | 2020 |
| Publisher: | American Chemical Society |
| ISSN: | 15237060 |
| Author Scopus IDs: | 57217139833 57217484113 55420218700 57215699430 57215694437 35319775800 |
| Author Affiliations: | Trost, B.M., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Hung, C.-I.J., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Mata, G., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Liu, Y., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Lu, Y., Department of Chemistry, Stanford University, Stanford, CA 94305, United States Gnanamani, E., Department of Chemistry, Stanford University, Stanford, CA 94305, United States |
| Funding Details: | We thank Dr. Jana Maclaren (Stanford University) for X-ray crystallographic analysis of compound 3b . We gratefully acknowledge the Swiss National Science Foundation (P300P2-171434) for financial support (fellowship to G.M.). |
| Corresponding Author: | Trost, B.M.; Department of Chemistry, Stanford UniversityUnited States; email: bmtrost@stanford.edu |
| Appears in Collections: | Journal Publications [CY] |
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