Literature DB >> 22693950

Highly enantioselective copper-catalyzed electrophilic trifluoromethylation of β-ketoesters.

Qing-Hai Deng1, Hubert Wadepohl, Lutz H Gade.   

Abstract

Enantioselective Cu-catalyzed trifluoromethylation of β-ketoesters using commercially available trifluoromethylating reagents is reported. A number of α-CF(3) β-ketoesters are obtained with up to 99% ee. The trifluoromethylated products were then transformed diastereoselectively to α-CF(3) β-hydroxyesters with two adjacent quaternary stereocenters via a Grignard reaction.

Entities:  

Year:  2012        PMID： 22693950     DOI： 10.1021/ja3039773

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  Synthesis and applications of α-trifluoromethylated alkylboron compounds.

Authors:  O Andreea Argintaru; DaWeon Ryu; Ioana Aron; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-07       Impact factor: 15.336

2.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

3.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

Authors:  Ekaterina V Vinogradova; Peter Müller; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

4.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

Review 5.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

6.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

7.  Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters.

Authors:  Łukasz Woźniak; John J Murphy; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2015-04-24       Impact factor: 15.419

Review 8.  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

9.  Towards an asymmetric organocatalytic α-cyanation of β-ketoesters.

Authors:  Raghunath Chowdhury; Johannes Schörgenhumer; Johanna Novacek; Mario Waser
Journal:  Tetrahedron Lett       Date:  2015-04-01       Impact factor: 2.415

10.  Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters.

Authors:  Abhijnan Ray Choudhury; Madhu Sudan Manna; Santanu Mukherjee
Journal:  Chem Sci       Date:  2017-08-02       Impact factor: 9.825
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