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.
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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 -