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Please use this identifier to cite or link to this item: 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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