Literature DB >> 26245887

Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters.

Ren-Rong Liu1, Shi-Chun Ye1, Chuan-Jun Lu1, Gui-Lin Zhuang1, Jian-Rong Gao1, Yi-Xia Jia2.   

Abstract

The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96 % ee) from readily available starting materials.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; carbenoids; chiral phosphoric acids; gold; indolinones

Mesh：

Substances：

Year:  2015        PMID： 26245887     DOI： 10.1002/anie.201504697

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


  11 in total

1.  Oxidative Coupling of 3-Oxindoles with Indoles and Arenes.

Authors:  Houng Kang; Adriana L Jemison; Erin Nigro; Marisa C Kozlowski
Journal:  ChemSusChem       Date:  2019-05-27       Impact factor: 8.928

2.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

3.  Palladium-catalyzed direct C(sp3)-H arylation of indole-3-ones with aryl halides: a novel and efficient method for the synthesis of nucleophilic 2-monoarylated indole-3-ones.

Authors:  Yong-Long Zhao; Yong-Qin Tang; Xing-Hai Fei; Tao Xiao; Ya-Dong Lu; Xiao-Zhong Fu; Bin He; Meng Zhou; Chun Li; Peng-Fei Xu; Yuan-Yong Yang
Journal:  RSC Adv       Date:  2018-07-16       Impact factor: 3.361

4.  A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones.

Authors:  Jian-Xiong An; Fen-Fen Yang; Pan Wang; Zhi-Cheng Gu; Yan Li; Lei Chen; Yong-Long Zhao; Bin He
Journal:  RSC Adv       Date:  2022-03-02       Impact factor: 3.361

5.  Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative dimerization of 2-aryl indoles and cross-addition with indoles.

Authors:  Anoop Singh; Satheeshvarma Vanaparthi; Sachin Choudhary; Rangan Krishnan; Indresh Kumar
Journal:  RSC Adv       Date:  2019-08-02       Impact factor: 3.361

6.  Synthesis of tetracyclic indolin-3-ones through Pd-catalyzed intramolecular deacetylative dearomatization of 3-acetoxy-indoles.

Authors:  Ren-Xiao Liang; Ke Wang; Ling-Jie Song; Wei-Jian Sheng; Yi-Xia Jia
Journal:  RSC Adv       Date:  2019-05-07       Impact factor: 3.361

7.  Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics.

Authors:  Jinhu Wei; Bei Cao; Chun-Wai Tse; Xiao-Yong Chang; Cong-Ying Zhou; Chi-Ming Che
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

8.  Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.

Authors:  Yingwei Zhao; Haoran Zhu; Siyoung Sung; Donald J Wink; Joseph M Zadrozny; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823

9.  Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones.

Authors:  Peng-Wei Xu; Jia-Kuan Liu; Lan Shen; Zhong-Yan Cao; Xiao-Li Zhao; Jun Yan; Jian Zhou
Journal:  Nat Commun       Date:  2017-11-20       Impact factor: 14.919

10.  Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones.

Authors:  Xue Yan; Ying-De Tang; Cheng-Shi Jiang; Xigong Liu; Hua Zhang
Journal:  Molecules       Date:  2020-01-20       Impact factor: 4.411
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