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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...

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Autores principales: Liu, Ming-Shang, Shu, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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