Abstract
Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I2 gave α,β-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, α-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, α-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynylbenzene afforded α,α'-bridged cyclopentenone compounds in good yields.
| Original language | English |
|---|---|
| Pages (from-to) | 9123-9134 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 53 |
| Issue number | 27 |
| DOIs | |
| Publication status | Published - Jul 7 1997 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO. / Takahashi, Tamotsu; Xi, Zhenfeng; Nishihara, Yasushi; Huo, Shouquan; Kasai, Kayoko; Aoyagi, Koichiro; Denisov, Victor; Negishi, Ei Ichi.
In: Tetrahedron, Vol. 53, No. 27, 07.07.1997, p. 9123-9134.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO
AU - Takahashi, Tamotsu
AU - Xi, Zhenfeng
AU - Nishihara, Yasushi
AU - Huo, Shouquan
AU - Kasai, Kayoko
AU - Aoyagi, Koichiro
AU - Denisov, Victor
AU - Negishi, Ei Ichi
PY - 1997/7/7
Y1 - 1997/7/7
N2 - Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I2 gave α,β-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, α-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, α-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynylbenzene afforded α,α'-bridged cyclopentenone compounds in good yields.
AB - Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I2 gave α,β-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, α-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, α-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynylbenzene afforded α,α'-bridged cyclopentenone compounds in good yields.
UR - http://www.scopus.com/inward/record.url?scp=0030912188&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030912188&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00612-1
DO - 10.1016/S0040-4020(97)00612-1
M3 - Article
AN - SCOPUS:0030912188
VL - 53
SP - 9123
EP - 9134
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 27
ER -