Abstract
An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 5156-5161 |
| Number of pages | 6 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 11 |
| Issue number | 31 |
| DOIs | |
| Publication status | Published - 2013 Aug 21 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Lee, Y. T., Lee, Y. T., Lee, C. J., Sheu, C. N., Lin, B. Y., Wang, J. H., & Lin, W. (2013). Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: Mechanism and theoretical analysis. Organic and Biomolecular Chemistry, 11(31), 5156-5161. https://doi.org/10.1039/c3ob40858b