Copper(I)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles

Haowen Ma; Jiajie Feng; Wei Zhou; Chen Chen; Zhuoji Deng; Fengtao Zhou; Yifan Ouyang; Xinhao Zhang; Qian Cai

doi:10.1039/D1OB01327K

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Copper(i)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles†

Haowen Ma,‡^a Jiajie Feng,‡^bc Wei Zhou,

^a Chen Chen,^a Zhuoji Deng,^a Fengtao Zhou,^a Yifan Ouyang,^a Xinhao Zhang

*^bc and Qian Cai

*^a

Author affiliations

* Corresponding authors

^a College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, China
E-mail: caiqian@jnu.eud.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 cooperative catalytic strategy is developed for a copper-catalyzed asymmetric intramolecular C-arylation reaction with ureas as the co-catalysts. By forming hydrogen bonds with 1,3-dicarbonyl structures, ureas can activate the substrates, stabilize the carbanion intermediates and the products, and fix the syn-configurations of 1,3-dicarbonyl structures. They help enhance the reactivity, prevent side reactions and improve the enantioselectivities.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D1OB01327K
Article type: Paper
Submitted: 07 Jul 2021
Accepted: 11 Aug 2021
First published: 13 Aug 2021

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Org. Biomol. Chem., 2021,19, 7480-7484

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Copper(I)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles

H. Ma, J. Feng, W. Zhou, C. Chen, Z. Deng, F. Zhou, Y. Ouyang, X. Zhang and Q. Cai, Org. Biomol. Chem., 2021, 19, 7480 DOI: 10.1039/D1OB01327K

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Organic & Biomolecular Chemistry

Copper(i)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles†

Abstract

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Copper(I)-catalyzed asymmetric intramolecular C-arylation with ureas as the additives: highly enantioselective formation of spirooxindoles

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