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Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones
We herein report the ammonium salt‐catalyzed synthesis of chiral 3,3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF(3)S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's b...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8050839/ https://www.ncbi.nlm.nih.gov/pubmed/33897314 http://dx.doi.org/10.1002/adsc.202100029 |
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author | Eitzinger, Andreas Otevrel, Jan Haider, Victoria Macchia, Antonio Massa, Antonio Faust, Kirill Spingler, Bernhard Berkessel, Albrecht Waser, Mario |
author_facet | Eitzinger, Andreas Otevrel, Jan Haider, Victoria Macchia, Antonio Massa, Antonio Faust, Kirill Spingler, Bernhard Berkessel, Albrecht Waser, Mario |
author_sort | Eitzinger, Andreas |
collection | PubMed |
description | We herein report the ammonium salt‐catalyzed synthesis of chiral 3,3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF(3)S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof‐of‐concept for the racemic synthesis of the analogous F‐containing products was obtained as well, giving access to one of the rare examples of a fairly stable α‐F‐α‐amino acid derivative. [Image: see text] |
format | Online Article Text |
id | pubmed-8050839 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-80508392021-04-21 Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones Eitzinger, Andreas Otevrel, Jan Haider, Victoria Macchia, Antonio Massa, Antonio Faust, Kirill Spingler, Bernhard Berkessel, Albrecht Waser, Mario Adv Synth Catal Updates We herein report the ammonium salt‐catalyzed synthesis of chiral 3,3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF(3)S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof‐of‐concept for the racemic synthesis of the analogous F‐containing products was obtained as well, giving access to one of the rare examples of a fairly stable α‐F‐α‐amino acid derivative. [Image: see text] John Wiley and Sons Inc. 2021-02-17 2021-03-29 /pmc/articles/PMC8050839/ /pubmed/33897314 http://dx.doi.org/10.1002/adsc.202100029 Text en © 2021 The Authors. Advanced Synthesis & Catalysis 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 | Updates Eitzinger, Andreas Otevrel, Jan Haider, Victoria Macchia, Antonio Massa, Antonio Faust, Kirill Spingler, Bernhard Berkessel, Albrecht Waser, Mario Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title | Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title_full | Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title_fullStr | Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title_full_unstemmed | Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title_short | Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF(3)S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones |
title_sort | enantioselective bifunctional ammonium salt‐catalyzed syntheses of 3‐cf(3)s‐, 3‐rs‐, and 3‐f‐substituted isoindolinones |
topic | Updates |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8050839/ https://www.ncbi.nlm.nih.gov/pubmed/33897314 http://dx.doi.org/10.1002/adsc.202100029 |
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