3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

Yi Ru Chen, Madhusudhan Reddy Ganapuram, Kai Hong Hsieh, Kai Han Chen, Praneeth Karanam, Sandip Sambhaji Vagh, Yan Cheng Liou, Wenwei Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)


A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.

Original languageEnglish
Pages (from-to)12702-12705
Number of pages4
JournalChemical Communications
Issue number90
Publication statusPublished - 2018

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • General Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry


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