Issue 15, 2021
From the journal:

Organic Chemistry Frontiers

Copper(i)–catalyzed intramolecular asymmetric C-arylation of acyclic β-ester amides: enantioselective formation of chiral oxindoles†

Zhuoji Deng,‡a   Jiajie Feng,‡bc   Fengtao Zhou,a   Yifan Ouyang,a   Haowen Ma,a   Wei Zhou, ORCID logo *a   Xinhao Zhang*bc  and  Qian Cai ORCID logo *a  

* Corresponding authors

a International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, China
E-mail: weizhou88@jnu.edu.cn, caiqian@jnu.edu.cn

b Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China
E-mail: zhangxinhao@pku.edu.cn

c Shenzhen Bay Laboratory, Shenzhen 518132, China

Abstract

A highly efficient intramolecular asymmetric C-arylation of acyclic β-ester amides is demonstrated. A CuI/chiral diamine ligand catalyzed reaction, with t-BuOLi as the necessary base in MeCN, afforded 3,3′-disubstituted chiral oxindoles with quaternary stereogenic carboncenters in high yields and good to excellent enantioselectivities.

Graphical abstract: Copper(i)–catalyzed intramolecular asymmetric C-arylation of acyclic β-ester amides: enantioselective formation of chiral oxindoles

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Article information

DOI
https://doi.org/10.1039/D1QO00568E
Article type
Research Article
Submitted
13 Apr 2021
Accepted
23 May 2021
First published
04 Jun 2021

Org. Chem. Front., 2021,8, 4211-4216

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Copper(I)–catalyzed intramolecular asymmetric C-arylation of acyclic β-ester amides: enantioselective formation of chiral oxindoles

Z. Deng, J. Feng, F. Zhou, Y. Ouyang, H. Ma, W. Zhou, X. Zhang and Q. Cai, Org. Chem. Front., 2021, 8, 4211 DOI: 10.1039/D1QO00568E

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