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学科主题: 有机化学
题名: Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion
其他题名: Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion
作者: Yuan XT(袁新婷) ; Liu K(刘鲲) ; Li CZ(李超忠)
通讯作者: 李超忠
刊名: J. Org. Chem.
发表日期: 2008
卷: 73, 期:16, 页:6166-6171
收录类别: SCI
部门归属: 中科院上海有机所
英文摘要: The substituent effect on the reactivity and regioselectivity of N-(4-pentenyl)amidyl radical cyclization was investigated. Exclusive 6-endo cyclization was observed for N-(4-pentenyl)amidyl radicals with internal vinylic heteroatom substitution (Cl, Br, I, OMe, SEt). The substituent on the carbonyl group also showed a significant influence on the reactivity of amidyl radicals, which increases in the order of Ph < Me < OEt. As a result, the photostimulated reactions of N-(4-halopent-4-enyl)amides and carbamates (X = Cl, Br, 1) with DIB/I-2 or Pb(OAc)(4)/I-2 led to the efficient and exclusive formation of the corresponding piperidines while those of N-(5-halopent-4-enyl)amides afforded the pyrrolidine products only. The halogen-substitution effect also allowed the 6-exo and 7-endo amidyl radical cyclization to proceed in a highly regioselective manner. The above experimental results, in combination with theoretical analyses, revealed that the lone pair-lone pair repulsion between the nitrogen radical and the vinylic heteroatom played an important role in controlling the regioselectivity of cyclization.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000258332500016
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22842
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Yuan XT,Liu K,Li CZ. Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion[J]. J. Org. Chem.,2008,73(16):6166-6171.
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