Literature DB >> 30478868

Enantioselective C(sp3 )-H Amidation of Thioamides Catalyzed by a CobaltIII /Chiral Carboxylic Acid Hybrid System.

Seiya Fukagawa1, Yoshimi Kato1, Ryo Tanaka1, Masahiro Kojima1, Tatsuhiko Yoshino1, Shigeki Matsunaga1.   

Abstract

Recent advances in Cpx MIII catalysis (M=Co, Rh, Ir) have enabled a variety of enantioselective C(sp2 )-H functionalization reactions, but enantioselective C(sp3 )-H functionalization is still largely unexplored. We describe an asymmetric C(sp3 )-H amidation of thioamides using an achiral CoIII /chiral carboxylic acid hybrid catalytic system, which provides easy and straightforward access to chiral β-amino thiocarbonyl and β-amino carbonyl building blocks with a quaternary carbon stereocenter.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; asymmetric catalysis; chiral carboxylic acids; cobalt; thioamide

Year:  2018        PMID： 30478868     DOI： 10.1002/anie.201812215

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors:  Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2019-07-29       Impact factor: 15.419

2.  Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation.

Authors:  Guangchen Li; Yangyang Xing; Hui Zhao; Jin Zhang; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-23       Impact factor: 15.336

Review 3.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

4.  Biocatalytic, Intermolecular C-H Bond Functionalization for the Synthesis of Enantioenriched Amides.

Authors:  Soumitra V Athavale; Shilong Gao; Zhen Liu; Sharath Chandra Mallojjala; Jennifer S Hirschi; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-13       Impact factor: 15.336

5.  Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.

Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-29       Impact factor: 16.823

6.  Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes.

Authors:  Kaj M van Vliet; Lara H Polak; Maxime A Siegler; Jarl Ivar van der Vlugt; Célia Fonseca Guerra; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2019-09-10       Impact factor: 15.419

7.  Thioketone-directed rhodium(I) catalyzed enantioselective C-H bond arylation of ferrocenes.

Authors:  Zhong-Jian Cai; Chen-Xu Liu; Qiang Wang; Qing Gu; Shu-Li You
Journal:  Nat Commun       Date:  2019-09-13       Impact factor: 14.919

8.  Harnessing sulfur and nitrogen in the cobalt(iii)-catalyzed unsymmetrical double annulation of thioamides: probing the origin of chemo- and regio-selectivity.

Authors:  Majji Shankar; Arijit Saha; Somratan Sau; Arghadip Ghosh; Vincent Gandon; Akhila K Sahoo
Journal:  Chem Sci       Date:  2021-03-19       Impact factor: 9.825

9.  Mapping Catalyst-Solvent Interplay in Competing Carboamination/Cyclopropanation Reactions.

Authors:  Matthew D Wodrich; Miyeon Chang; Simone Gallarati; Łukasz Woźniak; Nicolai Cramer; Clemence Corminboeuf
Journal:  Chemistry       Date:  2022-06-10       Impact factor: 5.020

10.  Insights into Cobalta(III/IV/II)-Electrocatalysis: Oxidation-Induced Reductive Elimination for Twofold C-H Activation.

Authors:  Tjark H Meyer; João C A Oliveira; Debasish Ghorai; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-05       Impact factor: 15.336
  10 in total

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