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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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
Pages (from-to)3407-3415
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number16
DOIs
Publication statusPublished - 2020 Aug 19

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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