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Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines
Alternative Title远程酯基调控选择性: 非对映选择性合成四环螺环吲哚啉
Zhu J(朱俊)1; Liang Y(梁勇)1; Wang LJ(王丽佳)1; Zheng ZB(郑中博)1; HOUK K N1; Tang Y(唐勇)1
2014
Source PublicationJ. Am. Chem. Soc.
Volume136Issue:19Pages:6900-6903
AbstractStereocontrol 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.
Subject Area金属有机化学
DOI10.1021/ja503117q
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Indexed BySCI
Language英语
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Cited Times:67[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39064
Collection金属有机化学国家重点实验室
Corresponding AuthorTang Y(唐勇)
Affiliation1.中科院上海有机化学研究所
2.美国加州大学洛杉矶分校
Recommended Citation
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.
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