抄録
C-C bond-forming carboxylation and cyclization of trimethyl(2-methylenebut-3-yn-1-yl)silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
| 元の言語 | English |
|---|---|
| ページ（範囲） | 5706-5709 |
| ページ数 | 4 |
| ジャーナル | Organic Letters |
| 巻 | 17 |
| 発行部数 | 22 |
| DOI | |
| 出版物ステータス | Published - 2015 11 20 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
これを引用
SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives. / Sekine, Kohei; Sadamitsu, Yuta; Yamada, Tohru.
：: Organic Letters, 巻 17, 番号 22, 20.11.2015, p. 5706-5709.研究成果: Article
}
TY - JOUR
T1 - SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives
AU - Sekine, Kohei
AU - Sadamitsu, Yuta
AU - Yamada, Tohru
PY - 2015/11/20
Y1 - 2015/11/20
N2 - C-C bond-forming carboxylation and cyclization of trimethyl(2-methylenebut-3-yn-1-yl)silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
AB - C-C bond-forming carboxylation and cyclization of trimethyl(2-methylenebut-3-yn-1-yl)silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
UR - http://www.scopus.com/inward/record.url?scp=84947996969&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84947996969&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5b03023
DO - 10.1021/acs.orglett.5b03023
M3 - Article
AN - SCOPUS:84947996969
VL - 17
SP - 5706
EP - 5709
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 22
ER -