Diastereoselective [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CF2HCHN2: syntheses of CF2H-containing spirooxindoles

Wen-Yong Han; Jia Zhao; Jian-Shu Wang; Guang-Yan Xiang; Ding-Lei Zhang; Mei Bai; Bao-Dong Cui; Nan-Wei Wan; Yong-Zheng Chen

doi:10.1039/C7OB01266G

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Diastereoselective [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CF₂HCHN₂: syntheses of CF₂H-containing spirooxindoles†

Wen-Yong Han,

*^a Jia Zhao,^a Jian-Shu Wang,^a Guang-Yan Xiang,^a Ding-Lei Zhang,^a Mei Bai,^a Bao-Dong Cui,^a Nan-Wei Wan^a and Yong-Zheng Chen

*^a

Author affiliations

* Corresponding authors

^a Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China
E-mail: hanwy@zmc.edu.cn, yzchen@zmc.edu.cn

Abstract

An efficient [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CF₂HCHN₂ for the syntheses of spirooxindoles has been developed. This methodology gives access to a range of relatively complex spirooxindoles featuring a CF₂H group and three contiguous stereogenic centers in up to 84% yield and 99 : 1 trans/cis.

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Article information

DOI: https://doi.org/10.1039/C7OB01266G
Article type: Paper
Submitted: 23 May 2017
Accepted: 13 Jun 2017
First published: 13 Jun 2017

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Org. Biomol. Chem., 2017,15, 5571-5578

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Diastereoselective [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CF₂HCHN₂: syntheses of CF₂H-containing spirooxindoles

W. Han, J. Zhao, J. Wang, G. Xiang, D. Zhang, M. Bai, B. Cui, N. Wan and Y. Chen, Org. Biomol. Chem., 2017, 15, 5571 DOI: 10.1039/C7OB01266G

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Organic & Biomolecular Chemistry