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 N1; 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. |
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