Synthesis of CF3-containing spiro-epoxyoxindoles via the Corey–Chaykovsky reaction of N-alkyl isatins with Ph2S+CH2CF3OTf−

Bin Cheng; Bing Zu; Yuntong Li; Cheng Tao; Chen Zhang; Renqi Wang; Yun Li; Hongbin Zhai

doi:10.1039/C8OB00602D

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Synthesis of CF₃-containing spiro-epoxyoxindoles via the Corey–Chaykovsky reaction of N-alkyl isatins with Ph₂S⁺CH₂CF₃OTf⁻†

Bin Cheng,

*^a Bing Zu,^a Yuntong Li,^a Cheng Tao,^a Chen Zhang,^a Renqi Wang,

^a Yun Li

^a and Hongbin Zhai

*^abc

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
E-mail: chengb@lzu.edu.cn

^b Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, China
E-mail: zhaihb@pkusz.edu.cn

^c Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China

Abstract

CF₃-containing spiro-epoxyoxindoles were successfully prepared via the Corey–Chaykovsky reaction of N-alkyl isatins with the ylide generated from Ph₂S⁺CH₂CF₃OTf⁻ with almost exclusive diastereoselectivity. Further derivatizations of these spiro-epoxyoxindoles were explored via a photochemical reaction or Lewis acid-promoted allylation.

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Article information

DOI: https://doi.org/10.1039/C8OB00602D
Article type: Communication
Submitted: 10 Mar 2018
Accepted: 17 Apr 2018
First published: 24 Apr 2018

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Org. Biomol. Chem., 2018,16, 3564-3567

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Synthesis of CF₃-containing spiro-epoxyoxindoles via the Corey–Chaykovsky reaction of N-alkyl isatins with Ph₂S⁺CH₂CF₃OTf⁻

B. Cheng, B. Zu, Y. Li, C. Tao, C. Zhang, R. Wang, Y. Li and H. Zhai, Org. Biomol. Chem., 2018, 16, 3564 DOI: 10.1039/C8OB00602D

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Organic & Biomolecular Chemistry