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

doi:10.6023/cjoc201903050

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1655-1664.DOI: 10.6023/cjoc201903050 Previous Articles Next Articles

Special Issue: 金属有机化学；碳氢活化合辑2018-2019

Articles

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^a, 刘慧慧^a, 刘小兵^a, 刘田田^b, 朱玉芹^b, 张安安^b, 王涛^b, 华远照^c, 王敏灿^c, 毛国梁^a, 刘澜涛^b,c

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 发布日期:2019-05-15
通讯作者: 毛国梁, 刘澜涛 E-mail:liult05@iccas.ac.cn;maoguoliang@nepu.edu.cn
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.

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

Yang Yun^a, Liu Huihui^a, Liu Xiaobing^a, Liu Tiantian^b, Zhu Yuqin^b, Zhang Anan^b, Wang Tao^b, Hua Yuanzhao^c, Wang Mincan^c, Mao Guoliang^a, Liu Lantao^b,c

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:2019-03-24 Revised:2019-05-10 Published:2019-05-15
Contact: 10.6023/cjoc201903050 E-mail:liult05@iccas.ac.cn;maoguoliang@nepu.edu.cn
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).

1. Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination.PDF(4816KB)

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]. Chin. J. Org. Chem., 2019, 39(6): 1655-1664.

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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

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

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