Issue 20, 2016
From the journal:

Chemical Communications

Asymmetric sequential Au(i)/chiral tertiary amine catalysis: an enone-formation/cyanosilylation sequence to synthesize optically active 3-alkenyloxindoles from diazooxindoles†

Yu-Lei Zhao,‡a   Zhong-Yan Cao,‡a   Xing-Ping Zeng,a   Jia-Meng Shi,b   Yi-Hua Yub  and  Jian Zhou*ac  

* 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 Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University, 3663N, Shanghai 200062, P. R. China

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

Abstract

An unprecedented sequential gold-catalyzed enone-formation and bifunctional tertiary amine mediated asymmetric cyanosilylation reaction is developed, allowing the highly enantioselective synthesis of 3-alkenyloxindoles from diazooxindoles, furans and trimethylsilyl cyanide (TMSCN).

Graphical abstract: Asymmetric sequential Au(i)/chiral tertiary amine catalysis: an enone-formation/cyanosilylation sequence to synthesize optically active 3-alkenyloxindoles from diazooxindoles

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Article information

DOI
https://doi.org/10.1039/C6CC00333H
Article type
Communication
Submitted
14 Jan 2016
Accepted
03 Feb 2016
First published
08 Feb 2016

Chem. Commun., 2016,52, 3943-3946

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Asymmetric sequential Au(I)/chiral tertiary amine catalysis: an enone-formation/cyanosilylation sequence to synthesize optically active 3-alkenyloxindoles from diazooxindoles

Y. Zhao, Z. Cao, X. Zeng, J. Shi, Y. Yu and J. Zhou, Chem. Commun., 2016, 52, 3943 DOI: 10.1039/C6CC00333H

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