A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes

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	A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes
	Zhou SL(周少林) ; Yan B(闫彬) ; Liu YH(刘元红)
刊名	J. Org. Chem.
	2005
卷号	70 期号:10 页码:4006-4012
ISSN号	0022-3263
其他题名	锆杂环戊烯与酰腈的直接插入反应：控制性合成高烯丙酮和多取代环戊二烯
通讯作者	刘元红
英文摘要	The direct reaction of aroyl cyanides with zirconacyclopentenes was achieved cleanly under controlled reaction conditions. This methodology provided an extremely efficient, one-pot, and high-yield route for the synthesis of homoallyl ketones when the reaction was carried out at -50 &DEG; C. Trapping of the zirconium intermediate by a variety of electrophiles afforded functionalized homoallyl ketones. Remarkably, the insertion reaction occurred with complete chemoselectivity, that means, the Zr-sp(3) carbon bond reacted preferentially, which is different from Cu-mediated elaboration of zirconacycles. Surprisingly, when the reaction was done at room temperature, 1,2,3-trisubstituted cyclopentadiene derivatives were readily formed in high yields. The direct insertion reaction of zirconacyclopentanes with acyl cyanides was also described. When bicyclic zirconacyclopentanes were used, cyclopentanol derivatives were obtained with high stereoselectivity.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo050152i
语种	英语
WOS记录号	WOS:000228983300030
公开日期	2013-03-11
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/24219]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 GB/T 7714	Zhou SL,Yan B,Liu YH. A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes[J]. J. Org. Chem.,2005,70(10):4006-4012.
APA	周少林,闫彬,&刘元红.(2005).A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes.J. Org. Chem.,70(10),4006-4012.
MLA	周少林,et al."A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes".J. Org. Chem. 70.10(2005):4006-4012.