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Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones.
Org Lett. 2007 Aug 30; 9(18):3707-10.OL

Abstract

The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee.

Authors+Show Affiliations

Mizuta S
Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Shibata N
No affiliation info available
Akiti S
No affiliation info available
Fujimoto H
No affiliation info available
Nakamura S
No affiliation info available
Toru T
No affiliation info available

MeSH

CatalysisChemistry, PharmaceuticalCinchona AlkaloidsKetonesMethylationMolecular StructureQuaternary Ammonium CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17691734

Citation

Mizuta, Satoshi, et al. "Cinchona alkaloids/TMAF Combination-catalyzed Nucleophilic Enantioselective Trifluoromethylation of Aryl Ketones." Organic Letters, vol. 9, no. 18, 2007, pp. 3707-10.
Mizuta S, Shibata N, Akiti S, et al. Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones. Org Lett. 2007;9(18):3707-10.
Mizuta, S., Shibata, N., Akiti, S., Fujimoto, H., Nakamura, S., & Toru, T. (2007). Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones. Organic Letters, 9(18), 3707-10.
Mizuta S, et al. Cinchona alkaloids/TMAF Combination-catalyzed Nucleophilic Enantioselective Trifluoromethylation of Aryl Ketones. Org Lett. 2007 Aug 30;9(18):3707-10. PubMed PMID: 17691734.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones. AU - Mizuta,Satoshi, AU - Shibata,Norio, AU - Akiti,Surendar, AU - Fujimoto,Hiroyuki, AU - Nakamura,Shuichi, AU - Toru,Takeshi, Y1 - 2007/08/10/ PY - 2007/8/19/pubmed PY - 2007/11/10/medline PY - 2007/8/19/entrez SP - 3707 EP - 10 JF - Organic letters JO - Org Lett VL - 9 IS - 18 N2 - The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17691734/Cinchona_alkaloids/TMAF_combination_catalyzed_nucleophilic_enantioselective_trifluoromethylation_of_aryl_ketones_ L2 - https://doi.org/10.1021/ol701791r DB - PRIME DP - Unbound Medicine ER -