Convenient preparative method of alpha,beta-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO

被引:67
作者
Takahashi, T [1 ]
Xi, ZF [1 ]
Nishihara, Y [1 ]
Huo, SQ [1 ]
Kasai, K [1 ]
Aoyagi, K [1 ]
Denisov, V [1 ]
Negishi, E [1 ]
机构
[1] HOKKAIDO UNIV,GRAD SCH PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1016/S0040-4020(97)00612-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I-2 gave alpha,beta-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, alpha-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyclopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:9123 / 9134
页数:12
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