Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et2Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines

Shiwei Yang; Guangling Bian; Zhongxiang Chen; Xiaohan Xia; Mi Zhou; Caiyan Cui; Ling Song

doi:10.1039/C7RA07692D

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Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(ii) chloride via Et₂Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines†

Shiwei Yang,^ab Guangling Bian,

*^a Zhongxiang Chen,^a Xiaohan Xia,^a Mi Zhou,^a Caiyan Cui^a and Ling Song*^ab

Author affiliations

* Corresponding authors

^a The Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, P. R. China
E-mail: songling@fjirsm.ac.cn, glb@fjirsm.ac.cn

^b University of Chinese Academy of Sciences, Beijing, P. R. China

Abstract

A highly efficient and practical approach to chiral quaternary 3-aminooxindoles was developed via Et₂Zn catalyzed diastereoselective addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines giving good to excellent yields and diastereoselectivities with broad substrates and reagent scopes promoted by zinc(II) chloride.

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Article information

DOI: https://doi.org/10.1039/C7RA07692D
Article type: Paper
Submitted: 13 Jul 2017
Accepted: 25 Jul 2017
First published: 03 Aug 2017
This article is Open Access

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RSC Adv., 2017,7, 38216-38219

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Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et₂Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines

S. Yang, G. Bian, Z. Chen, X. Xia, M. Zhou, C. Cui and L. Song, RSC Adv., 2017, 7, 38216 DOI: 10.1039/C7RA07692D

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