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 language | English |
|---|---|
| Pages (from-to) | 12702-12705 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 54 |
| Issue number | 90 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
ASJC Scopus subject areas
- Catalysis
- Electronic, Optical and Magnetic Materials
- Ceramics and Composites
- Chemistry(all)
- Surfaces, Coatings and Films
- Metals and Alloys
- Materials Chemistry
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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