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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...

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Autores principales: Eitzinger, Andreas, Otevrel, Jan, Haider, Victoria, Macchia, Antonio, Massa, Antonio, Faust, Kirill, Spingler, Bernhard, Berkessel, Albrecht, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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]
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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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