Abstract
The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.
| Original language | English |
|---|---|
| Pages (from-to) | 2299-2306 |
| Number of pages | 8 |
| Journal | Heterocycles |
| Volume | 94 |
| Issue number | 12 |
| DOIs | |
| Publication status | Published - Jan 1 2017 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Cite this
Hayakawa, I., Yamanaka, Y., Mitsudo, K., Ota, H., & Sakakura, A. (2017). Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions. Heterocycles, 94(12), 2299-2306. https://doi.org/10.3987/COM-17-13820