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 |
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ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions. / Hayakawa, Ichiro; Yamanaka, Yuji; Mitsudo, Koichi; Ota, Hiromi; Sakakura, Akira.
In: Heterocycles, Vol. 94, No. 12, 01.01.2017, p. 2299-2306.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions
AU - Hayakawa, Ichiro
AU - Yamanaka, Yuji
AU - Mitsudo, Koichi
AU - Ota, Hiromi
AU - Sakakura, Akira
PY - 2017/1/1
Y1 - 2017/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85037036285&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85037036285&partnerID=8YFLogxK
U2 - 10.3987/COM-17-13820
DO - 10.3987/COM-17-13820
M3 - Article
AN - SCOPUS:85037036285
VL - 94
SP - 2299
EP - 2306
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 12
ER -