Literature DB >> 30893497

Enantioselective Synthesis of C-N Axially Chiral N-Aryloxindoles by Asymmetric Rhodium-Catalyzed Dual C-H Activation.

Honghe Li1, Xiaoqiang Yan1, Jitan Zhang1, Weicong Guo1, Jijun Jiang1, Jun Wang1.   

Abstract

The first enantioselective Satoh-Miura-type reaction is reported. A variety of C-N axially chiral N-aryloxindoles have been enantioselectively synthesized by an asymmetric n class="Chemical">rhodium-catalyzed dual C-H activation reaction of N-aryloxindoles and alkynes. High yields and enantioselectivities were obtained (up to 99 % yield and up to 99 % ee). To date, it is also the first example of the asymmetric synthesis of C-N axially chiral compounds by such a C-H activation strategy.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; alkynes; axial chirality; heterocycles; rhodium

Year:  2019        PMID: 30893497     DOI: 10.1002/anie.201901619

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


  6 in total

1.  RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group.

Authors:  Lincong Sun; Yuyao Zhao; Bingxian Liu; Junbiao Chang; Xingwei Li
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

2.  Thioether-enabled palladium-catalyzed atroposelective C-H olefination for N-C and C-C axial chirality.

Authors:  Yanjun Li; Yan-Cheng Liou; Xinran Chen; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-03-10       Impact factor: 9.825

Review 3.  Asymmetric Synthesis of Axially Chiral C-N Atropisomers.

Authors:  Patricia Rodríguez-Salamanca; Rosario Fernández; Valentín Hornillos; José M Lassaletta
Journal:  Chemistry       Date:  2022-03-25       Impact factor: 5.020

Review 4.  Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.

Authors:  Xiao Xiao; Biao Chen; Yi-Ping Yao; Hai-Jie Zhou; Xu Wang; Neng-Zhong Wang; Fen-Er Chen
Journal:  Molecules       Date:  2022-10-04       Impact factor: 4.927

5.  Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.

Authors:  Xiaoze Bao; Jean Rodriguez; Damien Bonne
Journal:  Chem Sci       Date:  2019-11-20       Impact factor: 9.825

6.  Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves.

Authors:  Weiwei Luo; Zhicheng Sun; E H Nisala Fernando; Vladimir N Nesterov; Thomas R Cundari; Hong Wang
Journal:  Chem Sci       Date:  2020-07-09       Impact factor: 9.825

  6 in total

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