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

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7 Citations (Scopus)

Abstract

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
Volume54
Issue number90
DOIs
Publication statusPublished - 2018 Jan 1

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ASJC Scopus subject areas

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

Cite this

Chen, Y. R., Ganapuram, M. R., Hsieh, K. H., Chen, K. H., Karanam, P., Vagh, S. S., Liou, Y. C., & Lin, W. (2018). 3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition. Chemical Communications, 54(90), 12702-12705. https://doi.org/10.1039/c8cc07271j