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A controllable synthesis of homoallyl ketones and multiply substituted Cyclopentadienes by direct insertion of aroyl cyanides to zirconacyclopentenes
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
Zhou SL(周少林); Yan B(闫彬); Liu YH(刘元红)
2005
发表期刊J. Org. Chem.
ISSN0022-3263
卷号70期号:10页码:4006-4012
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 ° 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.
学科领域金属有机化学
部门归属中科院上海有机所金属有机化学国家重点实验室
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收录类别SCI
语种英语
WOS记录号WOS:000228983300030
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/24219
专题金属有机化学国家重点实验室
通讯作者Liu YH(刘元红)
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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.
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