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Issue 13, 2018
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NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C–F bond cleavage protocol

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Abstract

A chiral NHC-catalyzed cycloaddition of γ-fluoroenals is developed. The nucleophilic γ-carbon generated via C–F bond cleavage undergoes highly enantioselective cycloaddition (up to >99% ee) to isatins and provides 3′-spirocyclic oxindoles in good yields (up to 91%).

Graphical abstract: NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C–F bond cleavage protocol

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Publication details

The article was received on 18 Oct 2017, accepted on 07 Dec 2017 and first published on 07 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08048D
Citation: Chem. Commun., 2018,54, 1567-1570
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    NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C–F bond cleavage protocol

    J. Yan, K. Shi, C. Zhao, L. Ding, S. Jiang, L. Yang and G. Zhong, Chem. Commun., 2018, 54, 1567
    DOI: 10.1039/C7CC08048D

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