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Issue 19, 2018
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Synthesis of CF3-containing spiro-epoxyoxindoles via the Corey–Chaykovsky reaction of N-alkyl isatins with Ph2S+CH2CF3OTf

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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.

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

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Publication details

The article was received on 10 Mar 2018, accepted on 17 Apr 2018 and first published on 24 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00602D
Citation: 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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