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Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls
A widely applicable, practical, and scalable synthetic method for efficient ene‐type double oxidation of alkenes is reported via a two‐step alkenyl thianthrenium umpolung/Kornblum‐Ganem oxidation strategy. This chemo‐ and stereoselective procedure allows easy access to various α,β‐unsaturated carbon...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108043/ https://www.ncbi.nlm.nih.gov/pubmed/36408745 http://dx.doi.org/10.1002/anie.202214096 |
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author | Angyal, Péter Kotschy, András M. Dudás, Ádám Varga, Szilárd Soós, Tibor |
author_facet | Angyal, Péter Kotschy, András M. Dudás, Ádám Varga, Szilárd Soós, Tibor |
author_sort | Angyal, Péter |
collection | PubMed |
description | A widely applicable, practical, and scalable synthetic method for efficient ene‐type double oxidation of alkenes is reported via a two‐step alkenyl thianthrenium umpolung/Kornblum‐Ganem oxidation strategy. This chemo‐ and stereoselective procedure allows easy access to various α,β‐unsaturated carbonyls that may be otherwise difficult or cumbersome to synthesize by conventional methods. For α‐olefins, this metal‐free transformation can be tuned according to synthetic needs to produce either the elusive (Z)‐unsaturated aldehydes or their (E) counterparts. Moreover, this strategy has enabled streamlined synthesis of distinct butadienyl pheromones and kairomones. |
format | Online Article Text |
id | pubmed-10108043 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101080432023-04-18 Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls Angyal, Péter Kotschy, András M. Dudás, Ádám Varga, Szilárd Soós, Tibor Angew Chem Int Ed Engl Communications A widely applicable, practical, and scalable synthetic method for efficient ene‐type double oxidation of alkenes is reported via a two‐step alkenyl thianthrenium umpolung/Kornblum‐Ganem oxidation strategy. This chemo‐ and stereoselective procedure allows easy access to various α,β‐unsaturated carbonyls that may be otherwise difficult or cumbersome to synthesize by conventional methods. For α‐olefins, this metal‐free transformation can be tuned according to synthetic needs to produce either the elusive (Z)‐unsaturated aldehydes or their (E) counterparts. Moreover, this strategy has enabled streamlined synthesis of distinct butadienyl pheromones and kairomones. John Wiley and Sons Inc. 2022-12-02 2023-01-09 /pmc/articles/PMC10108043/ /pubmed/36408745 http://dx.doi.org/10.1002/anie.202214096 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Angyal, Péter Kotschy, András M. Dudás, Ádám Varga, Szilárd Soós, Tibor Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title | Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title_full | Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title_fullStr | Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title_full_unstemmed | Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title_short | Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene‐type Oxidation to Furnish α,β‐Unsaturated Carbonyls |
title_sort | intertwining olefin thianthrenation with kornblum/ganem oxidations: ene‐type oxidation to furnish α,β‐unsaturated carbonyls |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108043/ https://www.ncbi.nlm.nih.gov/pubmed/36408745 http://dx.doi.org/10.1002/anie.202214096 |
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