Literature DB >> 17691734

Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones.

Satoshi Mizuta1, Norio Shibata, Surendar Akiti, Hiroyuki Fujimoto, Shuichi Nakamura, Takeshi Toru.   

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.

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Year:  2007        PMID： 17691734     DOI： 10.1021/ol701791r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

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Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

4.  Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions.

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Journal:  J Am Chem Soc       Date:  2018-10-09       Impact factor: 15.419

Review 5.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

6.  Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides.

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Journal:  Beilstein J Org Chem       Date:  2018-01-19       Impact factor: 2.883

7.  Cs₂CO₃-Initiated Trifluoro-Methylation of Chalcones and Ketones for Practical Synthesis of Trifluoromethylated Tertiary Silyl Ethers.

Authors:  Cheng Dong; Xing-Feng Bai; Ji-Yuan Lv; Yu-Ming Cui; Jian Cao; Zhan-Jiang Zheng; Li-Wen Xu
Journal:  Molecules       Date:  2017-05-18       Impact factor: 4.411

8.  Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H reagents catalyzed by chiral quaternary ammonium salts.

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Journal:  Beilstein J Org Chem       Date:  2008-06-26       Impact factor: 2.883

9.  Anion-Initiated Trifluoromethylation by TMSCF3: Deconvolution of the Siliconate-Carbanion Dichotomy by Stopped-Flow NMR/IR.

Authors:  Craig P Johnston; Thomas H West; Ruth E Dooley; Marc Reid; Ariana B Jones; Edward J King; Andrew G Leach; Guy C Lloyd-Jones
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  9 in total

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