TiCl4/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds

Luyi Zhu; Peipei Yan; Lvye Zhang; Zhangtao Chen; Xiaofei Zeng; Guofu Zhong

doi:10.1039/C7RA09951G

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TiCl₄/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds†

Luyi Zhu,^a Peipei Yan,^a Lvye Zhang,^a Zhangtao Chen,^a Xiaofei Zeng

*^a and Guofu Zhong*^a

Author affiliations

* Corresponding authors

^a College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, P. R. China
E-mail: chemzxf@hznu.edu.cn, zgf@hznu.edu.cn

Abstract

A highly efficient Z-selective Knovenagel condensation reaction of isatins with nitroacetates mediated by TiCl₄ and DMAP was described. The desired 2-nitro-3-ylideneoxindole acetates were obtained in good to excellent stereoselectivities and yields. Other activated methylene derivatives as well as 4-methylbenzenesulfonamide could provide good results too. This method makes it possible to obtain various unreported 3-ylideneoxindole derivatives under mild reaction conditions.

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Article information

DOI: https://doi.org/10.1039/C7RA09951G
Article type: Paper
Submitted: 06 Sep 2017
Accepted: 25 Oct 2017
First published: 03 Nov 2017
This article is Open Access

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RSC Adv., 2017,7, 51352-51358

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TiCl₄/DMAP mediated Z-selective knovenagel condensation of isatins with nitroacetates and related compounds

L. Zhu, P. Yan, L. Zhang, Z. Chen, X. Zeng and G. Zhong, RSC Adv., 2017, 7, 51352 DOI: 10.1039/C7RA09951G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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