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学科主题: 金属有机化学
题名: A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity
其他题名: 一种对于手性磷酸催化的硝基烯烃与4,7-二氢吲哚的不对称傅克反应的理论探讨: 反应活性与选择性
作者: Zheng C(郑超) ; Sheng YF(盛益飞) ; Li YX(李玉学) ; You SL(游书力)
通讯作者: 李玉学 ; 游书力
刊名: Tetrahedron
发表日期: 2010
卷: 66, 期:15, 页:2875-2880
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: This article mainly focused on high level Density Functional Theory (DFT) studies on the chiral phosphoric acid-catalyzed Friedel-Crafts reactions between 4,7-dihydroindoles and nitroolefins. Firstly, the reactivities of 4,7-dihydroindole and indole in the chiral phosphoric acid-catalyzed Friedel-Crafts reactions with nitroolefin have been compared. The higher reactivity of 4,7-dihydroindole could be attributed to its higher HOMO energy as well as its more suitable trajectory to attack the nitroolefin in the transition state. Secondly, the origin of the enantioselectivity of the chiral phosphoric acid-catalyzed Friedel-Crafts reaction of 4,7-dihydroindole with nitroolefin has been studied using complete models on PBE1PBE/[6-311+G(d,p), 6-31G(d,p)] level. When (S)-1b was used as the catalyst, the enantioselectivity of the reaction is entirely controlled by the steric effect between the catalyst and the substrate. Whereas for catalyst (S)-1c the enantioselectivity is determined by the solvent effect. (C) 2010 Elsevier Ltd. All rights reserved.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000276490800012
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22522
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
Zheng C,Sheng YF,Li YX,et al. A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity[J]. Tetrahedron,2010,66(15):2875-2880.
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