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Stereoselective preparation of methylenecyclobutane-fused angular tetracyclic spiroindolines via photosensitized intramolecular [2+2] cycloaddition with allene
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| Title: | Stereoselective preparation of methylenecyclobutane-fused angular tetracyclic spiroindolines via photosensitized intramolecular [2+2] cycloaddition with allene |
| Authors: | Arai, Noriyoshi Browse this author →KAKEN DB | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Keywords: | Indole | | Allene | | Photoreaction | | [2+2] Cycloaddition |
| Issue Date: | 14-Nov-2019 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron Letters |
| Volume: | 60 |
| Issue: | 46 |
| Start Page: | 151252 |
| Publisher DOI: | 10.1016/j.tetlet.2019.151252 |
| Abstract: | Irradiation of 3-(hexa-4,5-dienyl)indole derivatives in the presence of 3',4'-dimethoxyacetophenone by a high-pressure mercury lamp through Pyrex glass gave the corresponding [2+2] cycloaddition products stereoselectively in high yields. The major product was a methylenecyclobutane-fused angular tetracyclic spiroindoline derivative produced by the [2+2] cycloaddition through a parallel orientation. The minor product was a hexahydromethanocarbazole derivative through a crossed orientation. Electron-withdrawing substituents, such as acyl or alkoxycarbonyl, on the indole nitrogen were suitable for this reaction. (C) 2019 Elsevier Ltd. All rights reserved. |
| Rights: | ©2019. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | | http://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/83278 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 新井 則義
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