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Photosensitized Intramolecular [2+2] Cycloaddition of 1H-Pyrrolo[2,3-b]pyridines Enabled by the Assistance of Lewis Acids
| Title: | Photosensitized Intramolecular [2+2] Cycloaddition of 1H-Pyrrolo[2,3-b]pyridines Enabled by the Assistance of Lewis Acids |
| Authors: | Arai, Noriyoshi Browse this author →KAKEN DB | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Issue Date: | 4-Dec-2020 |
| Publisher: | American Chemical Society |
| Journal Title: | Journal of organic chemistry |
| Volume: | 85 |
| Issue: | 23 |
| Start Page: | 15717 |
| End Page: | 15725 |
| Publisher DOI: | 10.1021/acs.joc.0c02231 |
| Abstract: | The [2+2] photocycloaddition of alkenyl-tethered 1H-pyrrolo[2,3-b]pyridine derivatives sensitized with 3',4'-dimethoxyacetophenone under irradiation by a high-pressure mercury lamp through Pyrex glass was dramatically accelerated by the addition of Lewis acids, preferably Mg(OTf)(2), to give the products stereoselectively in high yields. The reaction without a Lewis acid gave only small amounts of the [2+2] cycloaddition products. Conformational fixation of the substrates by coordination with a Lewis acid was presumed to facilitate the cycloaddition. |
| Rights: | This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Journal of organic chemistry, copyright c American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.0c02231. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/83422 |
| 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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