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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 6: 1655 - 1664

DOI: https://doi.org/10.6023/cjoc201903050

Articles

Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination

  • Yang Yun ,
  • Liu Huihui ,
  • Liu Xiaobing ,
  • Liu Tiantian ,
  • Zhu Yuqin ,
  • Zhang Anan ,
  • Wang Tao ,
  • Hua Yuanzhao ,
  • Wang Mincan ,
  • Mao Guoliang ,
  • Liu Lantao
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  • a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318;
    b College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000;
    c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received date: 2019-03-24

  Revised date: 2019-05-10

  Online published: 2019-05-15

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011).

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Abstract

Due to the lower configuration stability of vinylarenes, arsing from the relatively lower rotational barriers, their catalytic asymmetric synthesis remains a daunting task. Oxindoles moiety are privileged framework of natural products and building blocks of bioactive molecules as well as pharmaceuticals. The asymmetric synthesis of axial chiral vinylarenes fearturing oxindole moiety via sequential carbopalladation/C-H olefination from readily available materials with palladium catalysis has been developed. (4R,5R)-(-)-2,2-Dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL)-derived phosphoramidite gave products with good yield and moderate ee value. The erosion of optical purity was not observed even after heating the product for 10 h at 110℃, which indicates the excellent stability of the chiral axial.

Key words： asymmetric synthesis; axial chirality; vinyl-arenes; carbopalladation; C-H olefination; oxindole

Cite this article

Yang Yun , Liu Huihui , Liu Xiaobing , Liu Tiantian , Zhu Yuqin , Zhang Anan , Wang Tao , Hua Yuanzhao , Wang Mincan , Mao Guoliang , Liu Lantao . Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1655 -1664 . DOI: 10.6023/cjoc201903050

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