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Rapid Synthesis of β-Chiral Sulfones by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of Alkenes
[Image: see text] β-Chiral sulfones are substructures widespread in drug molecules and bioactive targets and serve as important chiral synthons in organic synthesis yet are challenging to access. Herein, a three-component strategy enabled by visible-light- and Ni-catalyzed sulfonylalkenylation of st...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10207110/ https://www.ncbi.nlm.nih.gov/pubmed/37234126 http://dx.doi.org/10.1021/jacsau.3c00069 |
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author | Liu, Ming-Shang Shu, Wei |
author_facet | Liu, Ming-Shang Shu, Wei |
author_sort | Liu, Ming-Shang |
collection | PubMed |
description | [Image: see text] β-Chiral sulfones are substructures widespread in drug molecules and bioactive targets and serve as important chiral synthons in organic synthesis yet are challenging to access. Herein, a three-component strategy enabled by visible-light- and Ni-catalyzed sulfonylalkenylation of styrenes for the synthesis of enantioenriched β-chiral sulfones has been developed. This dual-catalysis strategy allows for one-step skeletal assembly along with the control of enantioselectivity in the presence of a chiral ligand, providing an efficient and straightforward access to enantioenriched β-alkenyl sulfones from easily available and simple starting materials. Mechanistic investigations reveal that the reaction undergoes a chemoselective radical addition over two alkenes followed by a Ni-intercepted asymmetric C(sp(3))–C(sp(2)) coupling with alkenyl halides. |
format | Online Article Text |
id | pubmed-10207110 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-102071102023-05-25 Rapid Synthesis of β-Chiral Sulfones by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of Alkenes Liu, Ming-Shang Shu, Wei JACS Au [Image: see text] β-Chiral sulfones are substructures widespread in drug molecules and bioactive targets and serve as important chiral synthons in organic synthesis yet are challenging to access. Herein, a three-component strategy enabled by visible-light- and Ni-catalyzed sulfonylalkenylation of styrenes for the synthesis of enantioenriched β-chiral sulfones has been developed. This dual-catalysis strategy allows for one-step skeletal assembly along with the control of enantioselectivity in the presence of a chiral ligand, providing an efficient and straightforward access to enantioenriched β-alkenyl sulfones from easily available and simple starting materials. Mechanistic investigations reveal that the reaction undergoes a chemoselective radical addition over two alkenes followed by a Ni-intercepted asymmetric C(sp(3))–C(sp(2)) coupling with alkenyl halides. American Chemical Society 2023-04-27 /pmc/articles/PMC10207110/ /pubmed/37234126 http://dx.doi.org/10.1021/jacsau.3c00069 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Liu, Ming-Shang Shu, Wei Rapid Synthesis of β-Chiral Sulfones by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of Alkenes |
title | Rapid Synthesis of
β-Chiral Sulfones
by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of
Alkenes |
title_full | Rapid Synthesis of
β-Chiral Sulfones
by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of
Alkenes |
title_fullStr | Rapid Synthesis of
β-Chiral Sulfones
by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of
Alkenes |
title_full_unstemmed | Rapid Synthesis of
β-Chiral Sulfones
by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of
Alkenes |
title_short | Rapid Synthesis of
β-Chiral Sulfones
by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of
Alkenes |
title_sort | rapid synthesis of
β-chiral sulfones
by ni-organophotocatalyzed enantioselective sulfonylalkenylation of
alkenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10207110/ https://www.ncbi.nlm.nih.gov/pubmed/37234126 http://dx.doi.org/10.1021/jacsau.3c00069 |
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