Issue 12, 2016
From the journal:

Chemical Communications

Sequential Au(i)/chiral tertiary amine catalysis: a tandem C–H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles†

Zhong-Yan Cao,‡a   Yu-Lei Zhao‡a  and  Jian Zhou*ab  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China
E-mail: jzhou@chem.ecnu.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

We report an unprecedented sequential Au(I)/bifunctional tertiary amine catalysis, which enables a tandem C–H functionalization of weak nucleophiles (anisoles or thiophenes) and asymmetric Michael addition for the highly enantioselective synthesis of quaternary oxindoles from diazooxindoles and nitroenynes.

Graphical abstract: Sequential Au(i)/chiral tertiary amine catalysis: a tandem C–H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles

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Article information

DOI
https://doi.org/10.1039/C5CC10096H
Article type
Communication
Submitted
08 Dec 2015
Accepted
23 Dec 2015
First published
23 Dec 2015

Chem. Commun., 2016,52, 2537-2540

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Sequential Au(I)/chiral tertiary amine catalysis: a tandem C–H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles

Z. Cao, Y. Zhao and J. Zhou, Chem. Commun., 2016, 52, 2537 DOI: 10.1039/C5CC10096H

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