Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines

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	Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines
	Zhu J(朱俊)1; Liang Y(梁勇)1; Wang LJ(王丽佳)1; Zheng ZB(郑中博)1; HOUK K N 1; Tang Y(唐勇)1
刊名	J. Am. Chem. Soc.
	2014
卷号	136 期号:19 页码:6900-6903
其他题名	远程酯基调控选择性: 非对映选择性合成四环螺环吲哚啉
通讯作者	唐勇
英文摘要	Stereocontrol in the synthesis of structurally complex molecules, especially those with all-carbon quaternary stereocenters, remains a challenge. Here, we reported the preparation of a class of tetracyclic cyclopenta-fused spiroindoline skeletons through Cu(II)catalyzed intramolecular [3 + 2] annulation reactions of donor-acceptor cyclopropanes with indoles. Both cis- and trans-diastereomers of tetracyclic spiroindolines are accessed with high selectivities by altering the remote ester groups of cyclopropanes. The origins of this stereocontrol are identified using DFT calculations: attractive interactions between the ester group and arene favor the generation of the trans isomer, while the formation of the cis isomer is preferred when steric repulsions become predominant.
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/ja503117q
语种	英语
内容类型	期刊论文
源URL	[http://ir.sioc.ac.cn/handle/331003/39064]
专题	上海有机化学研究所_金属有机化学国家重点实验室
作者单位	1.中科院上海有机化学研究所 2.美国加州大学洛杉矶分校
推荐引用方式 GB/T 7714	Zhu J,Liang Y,Wang LJ,et al. Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines[J]. J. Am. Chem. Soc.,2014,136(19):6900-6903.
APA	朱俊,梁勇,王丽佳,郑中博,HOUK K N,&唐勇.(2014).Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines.J. Am. Chem. Soc.,136(19),6900-6903.
MLA	朱俊,et al."Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines".J. Am. Chem. Soc. 136.19(2014):6900-6903.