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

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

研究论文

碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成

  • 杨云 ,
  • 刘慧慧 ,
  • 刘小兵 ,
  • 刘田田 ,
  • 朱玉芹 ,
  • 张安安 ,
  • 王涛 ,
  • 华远照 ,
  • 王敏灿 ,
  • 毛国梁 ,
  • 刘澜涛
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  • a 东北石油大学化学化工学院 大庆 163318;
    b 商丘师范学院化学化工学院 商丘 476000;
    c 郑州大学化学与分子工程学院 郑州 450001

收稿日期: 2019-03-24

  修回日期: 2019-05-10

  网络出版日期: 2019-05-15

基金资助

国家自然科学基金（No.21572126）、河南省高校科技创新人才基金（No.14HASTIT016）、河南省科技创新杰出人才（No.2018JQ0011）资助项目.

收起

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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摘要

由于较低的旋转能垒，轴手性烯基芳烃衍生物的催化不对称合成存在很大挑战.氧化吲哚是天然产物的重要骨架，也是生物活性分子及药物的重要合成子.作者通过碳钯化/C-H键的烯基化串联反应实现了含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成.（4R，5R）-2，2-二甲基-α，α，α'，α'-四苯基-1，3-二氧戊环-4，5-二甲醇（TADDOL）衍生的亚膦酰胺配体给出了较好的产率和中等的对映选择性.产物在110℃加热10 h后ee值没有降低，表明其手性轴具有很好的热稳定性.

关键词： 不对称合成; 轴手性; 烯基芳烃; 碳钯化; C-H键烯基化; 氧化吲哚

本文引用格式

杨云 , 刘慧慧 , 刘小兵 , 刘田田 , 朱玉芹 , 张安安 , 王涛 , 华远照 , 王敏灿 , 毛国梁 , 刘澜涛 . 碳钯化/C-H烯基化串联反应:含氧化吲哚类结构单元的轴手性烯基芳烃的不对称合成[J]. 有机化学, 2019 , 39(6) : 1655 -1664 . DOI: 10.6023/cjoc201903050

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

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