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Stereoselective construction of cycloheptene-fused indoline frameworks through photosensitised formal [5+2] cycloaddition
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| Title: | Stereoselective construction of cycloheptene-fused indoline frameworks through photosensitised formal [5+2] cycloaddition |
| Authors: | Arai, Noriyoshi Browse this author →KAKEN DB | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Keywords: | Indole | | Indoline | | Photoreaction | | Cycloaddition | | Fused ring frameworks |
| Issue Date: | 5-Jan-2022 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron Letters |
| Volume: | 88 |
| Start Page: | 153588 |
| Publisher DOI: | 10.1016/j.tetlet.2021.153588 |
| Abstract: | Irradiation of 1-acylindole derivatives that possess a vinylcyclopropane moiety at the end of the acyl side chain by a high-pressure mercury lamp through Pyrex glass under sensitization of an aromatic ketone gave the corresponding cyclised products stereoselectively in high yields. The distribution of the products was highly dependent on the substituents on the cyclopropane ring. In the case of a simple cyclopropane, the product was a mixture of ring-expanded cycloheptene-fused indoline and all -cis-fused cyclopropylcyclobutane-fused indoline through [2 + 2] cycloaddition, while cycloheptene-fused indolines were predominantly produced via formal [5 + 2] cyclisation in the case of substituted cyclopropanes. In particular, the product selectivity was substantially high in the case of silylcyclopropane. |
| Rights: | © 2021. 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 |
| URI: | http://hdl.handle.net/2115/90868 |
| 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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