Literature DB >> 30152915

Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO2 to Generate α,α-Disubstituted α-Amino Acids.

Tao Ju1, Qiang Fu1,2, Jian-Heng Ye1, Zhen Zhang1, Li-Li Liao1, Si-Shun Yan1, Xing-Yang Tian1, Shu-Ping Luo3, Jing Li1, Da-Gang Yu1,4.   

Abstract

The first catalytic hydrocarboxylation of enamides and imines with CO2 to generate valuable α,α-disubstituted α-amino acids is reported. Notably, excellent chemo- and regio-selectivity are achieved, significantly different from previous reports on β-carboxylation of enamides, homocoupling or reduction of imines. Moreover, this transition-metal-free procedure exhibits low loading of an inexpensive catalyst, easily available substrates, mild reaction conditions, high efficiency, facile scalability and easy product derivatization, providing great potential for application in organic synthesis, pharmaceutical chemistry, and biochemistry.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbon dioxide; homogeneous catalysis; hydrocarboxylation; selectivity; α,α-disubstituted α-amino acids

Year:  2018        PMID: 30152915     DOI: 10.1002/anie.201806874

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


  8 in total

1.  Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2.

Authors:  Guang-Mei Cao; Xin-Long Hu; Li-Li Liao; Si-Shun Yan; Lei Song; Jason J Chruma; Li Gong; Da-Gang Yu
Journal:  Nat Commun       Date:  2021-06-03       Impact factor: 14.919

Review 2.  Carbon dioxide photoreduction in prebiotic environments.

Authors:  Dhanalakshmi Vadivel; Francesco Ferraro; Daniele Merli; Daniele Dondi
Journal:  Photochem Photobiol Sci       Date:  2022-02-02       Impact factor: 4.328

3.  Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids.

Authors:  Xinyuan Fan; Xu Gong; Mengyue Ma; Rui Wang; Patrick J Walsh
Journal:  Nat Commun       Date:  2018-11-22       Impact factor: 14.919

Review 4.  Toward ideal carbon dioxide functionalization.

Authors:  Yang Yang; Ji-Woong Lee
Journal:  Chem Sci       Date:  2019-02-20       Impact factor: 9.825

Review 5.  Reductive radical-polar crossover: traditional electrophiles in modern radical reactions.

Authors:  Lena Pitzer; J Luca Schwarz; Frank Glorius
Journal:  Chem Sci       Date:  2019-08-16       Impact factor: 9.825

6.  Rhodium(iii)-catalyzed annulation of enamides with sulfoxonium ylides toward isoquinolines.

Authors:  Chao Hong; Shuling Yu; Zhanxiang Liu; Yuhong Zhang
Journal:  RSC Adv       Date:  2021-03-19       Impact factor: 3.361

7.  An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C-H Bond.

Authors:  Saiwen Liu; Ru Chen; Guowen He; Jin Zhang
Journal:  Molecules       Date:  2020-03-27       Impact factor: 4.411

Review 8.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336

  8 in total

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