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Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones
3‐Substituted quinoxalin‐2(1H)‐ones and various aryl‐substituted or tethered olefins underwent an enantioselective, inter‐ or intramolecular aza Paternò–Büchi reaction upon irradiation at λ=420 nm in the presence of a chiral sensitizer (10 mol %). For the intermolecular reaction with 1‐arylethenes a...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898282/ https://www.ncbi.nlm.nih.gov/pubmed/33084097 http://dx.doi.org/10.1002/anie.202013276 |
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author | Li, Xinyao Großkopf, Johannes Jandl, Christian Bach, Thorsten |
author_facet | Li, Xinyao Großkopf, Johannes Jandl, Christian Bach, Thorsten |
author_sort | Li, Xinyao |
collection | PubMed |
description | 3‐Substituted quinoxalin‐2(1H)‐ones and various aryl‐substituted or tethered olefins underwent an enantioselective, inter‐ or intramolecular aza Paternò–Büchi reaction upon irradiation at λ=420 nm in the presence of a chiral sensitizer (10 mol %). For the intermolecular reaction with 1‐arylethenes as olefin components, the scope of the reaction was studied (14 examples, 50–99 % yield, 86–98 % ee). The absolute and relative configuration of the products were elucidated by single‐crystal X‐ray crystallography. The reaction is suggested to occur by triplet energy transfer in a hydrogen‐bonded 1:1 complex between the imine substrate and the catalyst. The intramolecular cycloaddition, consecutive reactions of the product azetidines, and an alternative reaction mode of quinoxalinones were investigated in preliminary experiments. |
format | Online Article Text |
id | pubmed-7898282 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-78982822021-03-03 Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones Li, Xinyao Großkopf, Johannes Jandl, Christian Bach, Thorsten Angew Chem Int Ed Engl Communications 3‐Substituted quinoxalin‐2(1H)‐ones and various aryl‐substituted or tethered olefins underwent an enantioselective, inter‐ or intramolecular aza Paternò–Büchi reaction upon irradiation at λ=420 nm in the presence of a chiral sensitizer (10 mol %). For the intermolecular reaction with 1‐arylethenes as olefin components, the scope of the reaction was studied (14 examples, 50–99 % yield, 86–98 % ee). The absolute and relative configuration of the products were elucidated by single‐crystal X‐ray crystallography. The reaction is suggested to occur by triplet energy transfer in a hydrogen‐bonded 1:1 complex between the imine substrate and the catalyst. The intramolecular cycloaddition, consecutive reactions of the product azetidines, and an alternative reaction mode of quinoxalinones were investigated in preliminary experiments. John Wiley and Sons Inc. 2020-12-01 2021-02-01 /pmc/articles/PMC7898282/ /pubmed/33084097 http://dx.doi.org/10.1002/anie.202013276 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Li, Xinyao Großkopf, Johannes Jandl, Christian Bach, Thorsten Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title | Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title_full | Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title_fullStr | Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title_full_unstemmed | Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title_short | Enantioselective, Visible Light Mediated Aza Paternò–Büchi Reactions of Quinoxalinones |
title_sort | enantioselective, visible light mediated aza paternò–büchi reactions of quinoxalinones |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898282/ https://www.ncbi.nlm.nih.gov/pubmed/33084097 http://dx.doi.org/10.1002/anie.202013276 |
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