Issue 86, 2022
From the journal:

Chemical Communications

Catalytic enantioselective hydrophosphinylation of in situ-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles†

Yun-Qing Jia,abc   Jian-Qiang Zhao, ORCID logo *b   Zhen-Hua Wang, ORCID logo b   Yong You, ORCID logo b   Yan-Ping Zhang,b   Xin Jin,d   Ming-Qiang Zhou,ac   Zhen-Zhen Geac  and  Wei-Cheng Yuan ORCID logo *ab  

* Corresponding authors

a National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China
E-mail: yuanwc@cioc.ac.cn

b Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, China
E-mail: zhaojianqiang@cdu.edu.cn

c University of Chinese Academy of Sciences, Beijing, China

d Zhejiang Jinhua Conba Bio-Pharm. Co. Ltd, Jinhua, China

Abstract

An efficient organocatalyzed enantioselective hydrophosphinylation of indole-derived vinylogous imines generated in situ from sulfonyl indoles has been developed. Using quinine-derived bifunctional thiourea as the catalyst, a wide range of structurally diverse chiral 3-(1-diphenylphosphoryl-arylmethyl)indoles were obtained with good to excellent results (up to 99% yield and 99% ee). This method represents the first example of the catalytic asymmetric Michael addition of phosphine oxides to vinylogous imine intermediates.

Graphical abstract: Catalytic enantioselective hydrophosphinylation of in situ-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles

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Article information

DOI
https://doi.org/10.1039/D2CC04763B
Article type
Communication
Submitted
29 Aug 2022
Accepted
28 Sep 2022
First published
29 Sep 2022

Chem. Commun., 2022,58, 12062-12065

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Catalytic enantioselective hydrophosphinylation of in situ-generated indole-derived vinylogous imines to access 3-(1-diphenylphosphoryl-arylmethyl)indoles

Y. Jia, J. Zhao, Z. Wang, Y. You, Y. Zhang, X. Jin, M. Zhou, Z. Ge and W. Yuan, Chem. Commun., 2022, 58, 12062 DOI: 10.1039/D2CC04763B

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