Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds

We report herein a new method for the synthesis of densely functionalized chiral allyl SCF(3), SCF(2)R, SCN and SAr species with a separate CF(3) functionality. The synthetic approach is based on selenium‐catalyzed sulfenofunctionalization of chiral α‐CF(3) allylboronic acids. The reactions proceede...

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Detalles Bibliográficos
Autores principales: Wang, Qiang, Nilsson, Tomas, Eriksson, Lars, Szabó, Kálmán J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828052/
https://www.ncbi.nlm.nih.gov/pubmed/36152310
http://dx.doi.org/10.1002/anie.202210509
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author Wang, Qiang
Nilsson, Tomas
Eriksson, Lars
Szabó, Kálmán J.
author_facet Wang, Qiang
Nilsson, Tomas
Eriksson, Lars
Szabó, Kálmán J.
author_sort Wang, Qiang
collection PubMed
description We report herein a new method for the synthesis of densely functionalized chiral allyl SCF(3), SCF(2)R, SCN and SAr species with a separate CF(3) functionality. The synthetic approach is based on selenium‐catalyzed sulfenofunctionalization of chiral α‐CF(3) allylboronic acids. The reactions proceeded with remarkably high stereo‐, diastereo‐ and site‐selectivity, based on the formation of a stable thiiranium ion followed by rapid deborylative ring opening.
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spelling pubmed-98280522023-01-10 Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds Wang, Qiang Nilsson, Tomas Eriksson, Lars Szabó, Kálmán J. Angew Chem Int Ed Engl Research Articles We report herein a new method for the synthesis of densely functionalized chiral allyl SCF(3), SCF(2)R, SCN and SAr species with a separate CF(3) functionality. The synthetic approach is based on selenium‐catalyzed sulfenofunctionalization of chiral α‐CF(3) allylboronic acids. The reactions proceeded with remarkably high stereo‐, diastereo‐ and site‐selectivity, based on the formation of a stable thiiranium ion followed by rapid deborylative ring opening. John Wiley and Sons Inc. 2022-10-17 2022-11-14 /pmc/articles/PMC9828052/ /pubmed/36152310 http://dx.doi.org/10.1002/anie.202210509 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 Research Articles
Wang, Qiang
Nilsson, Tomas
Eriksson, Lars
Szabó, Kálmán J.
Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title_full Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title_fullStr Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title_full_unstemmed Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title_short Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF(3), SCF(2)R, SCN and SAr Compounds
title_sort sulfenofunctionalization of chiral α‐trifluoromethyl allylboronic acids: asymmetric synthesis of scf(3), scf(2)r, scn and sar compounds
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828052/
https://www.ncbi.nlm.nih.gov/pubmed/36152310
http://dx.doi.org/10.1002/anie.202210509
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