Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction

Min Wang, Ping Yao Tseng, Woei Jye Chi, Sundaram Suresh, Athukuri Edukondalu, Yi Ru Chen, Wenwei Lin

    Research output: Contribution to journalArticlepeer-review

    Abstract

    An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acceptors and further regio/chemoselective reaction that preferentially resulted in spiro systems and fused cyclopentanes in a diversity-oriented manner. The 1,6-addition/aldol and 1,6-addition/vinylogous Michael addition cascade processes were controlled by different base/solvent systems to the predominant formation of one of the two carbocyclic compounds. (Figure presented.).

    Original languageEnglish
    JournalAdvanced Synthesis and Catalysis
    DOIs
    Publication statusAccepted/In press - 2020

    Keywords

    • 1,6-addition
    • aldol reaction
    • Diversity-oriented synthesis
    • spiro and fused systems
    • vinylogous Michael addition

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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