| 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 Publication | J. Am. Chem. Soc.
 |
| Volume | 136Issue:19Pages:6900-6903 |
| Abstract | 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. |
| Subject Area | 金属有机化学 |
| DOI | 10.1021/ja503117q |
| URL | 查看原文 |
| Indexed By | SCI |
| Language | 英语 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.sioc.ac.cn/handle/331003/39064 |
| Collection | 金属有机化学国家重点实验室 |
| Corresponding Author | Tang Y(唐勇) |
| Affiliation | 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 |
| 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. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| 2014242.pdf（845KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | Application Full Text | |
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