A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity

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	A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity
	Zheng C(郑超) ; Sheng YF(盛益飞) ; Li YX(李玉学) ; You SL(游书力)
刊名	Tetrahedron
	2010
卷号	66 期号:15 页码:2875-2880
ISSN号	0040-4020
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
通讯作者	李玉学 ; 游书力
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.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1016/j.tet.2010.02.031
语种	英语
WOS记录号	WOS:000276490800012
公开日期	2013-03-04
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/22522]
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	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.
APA	郑超,盛益飞,李玉学,&游书力.(2010).A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity.Tetrahedron,66(15),2875-2880.
MLA	郑超,et al."A theoretical investigation into chiral phosphoric acid-catalyzed asymmetric Friedel-Crafts reactions of nitroolefins and 4,7-dihydroindoles: reactivity and enantioselectivity".Tetrahedron 66.15(2010):2875-2880.