Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary

[Image: see text] Sulfonimidamides (SIAs) and sulfoximines (SOIs) have attracted attention due to their potential in agriculture and in medicinal chemistry as bioisosteres of biologically active compounds, and new synthetic methods are needed to access and explore these compounds. Herein, we present...

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Autores principales: Proietti, Giampiero, Kuzmin, Julius, Temerdashev, Azamat Z., Dinér, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650101/
https://www.ncbi.nlm.nih.gov/pubmed/34766772
http://dx.doi.org/10.1021/acs.joc.1c02241
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author Proietti, Giampiero
Kuzmin, Julius
Temerdashev, Azamat Z.
Dinér, Peter
author_facet Proietti, Giampiero
Kuzmin, Julius
Temerdashev, Azamat Z.
Dinér, Peter
author_sort Proietti, Giampiero
collection PubMed
description [Image: see text] Sulfonimidamides (SIAs) and sulfoximines (SOIs) have attracted attention due to their potential in agriculture and in medicinal chemistry as bioisosteres of biologically active compounds, and new synthetic methods are needed to access and explore these compounds. Herein, we present a light-promoted generation of perfluorinated aromatic nitrenes, from perfluorinated azides, that subsequently are allowed to react with sulfinamides and sulfoxides, generating achiral and chiral SIAs and SOIs. One of the enantiopure SIAs was evaluated as a novel chiral auxiliary in Grignard additions to the imines yielding the product in up to 96:4 diastereomeric ratio.
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spelling pubmed-86501012021-12-08 Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary Proietti, Giampiero Kuzmin, Julius Temerdashev, Azamat Z. Dinér, Peter J Org Chem [Image: see text] Sulfonimidamides (SIAs) and sulfoximines (SOIs) have attracted attention due to their potential in agriculture and in medicinal chemistry as bioisosteres of biologically active compounds, and new synthetic methods are needed to access and explore these compounds. Herein, we present a light-promoted generation of perfluorinated aromatic nitrenes, from perfluorinated azides, that subsequently are allowed to react with sulfinamides and sulfoxides, generating achiral and chiral SIAs and SOIs. One of the enantiopure SIAs was evaluated as a novel chiral auxiliary in Grignard additions to the imines yielding the product in up to 96:4 diastereomeric ratio. American Chemical Society 2021-11-12 2021-12-03 /pmc/articles/PMC8650101/ /pubmed/34766772 http://dx.doi.org/10.1021/acs.joc.1c02241 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Proietti, Giampiero
Kuzmin, Julius
Temerdashev, Azamat Z.
Dinér, Peter
Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title_full Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title_fullStr Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title_full_unstemmed Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title_short Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary
title_sort accessing perfluoroaryl sulfonimidamides and sulfoximines via photogenerated perfluoroaryl nitrenes: synthesis and application as a chiral auxiliary
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650101/
https://www.ncbi.nlm.nih.gov/pubmed/34766772
http://dx.doi.org/10.1021/acs.joc.1c02241
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