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Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides

[Image: see text] Sulfoximines provide aza-analogues of sulfones, with potentially improved properties for medicinal chemistry. The sulfoximine nitrogen also provides an additional vector for the inclusion of other functionality. Here, we report improved conditions for rhodium catalyzed synthesis of...

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Autores principales: Zhong, Zhenhao, Chesti, Julian, Armstrong, Alan, Bull, James A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724092/
https://www.ncbi.nlm.nih.gov/pubmed/36379008
http://dx.doi.org/10.1021/acs.joc.2c02083
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author Zhong, Zhenhao
Chesti, Julian
Armstrong, Alan
Bull, James A.
author_facet Zhong, Zhenhao
Chesti, Julian
Armstrong, Alan
Bull, James A.
author_sort Zhong, Zhenhao
collection PubMed
description [Image: see text] Sulfoximines provide aza-analogues of sulfones, with potentially improved properties for medicinal chemistry. The sulfoximine nitrogen also provides an additional vector for the inclusion of other functionality. Here, we report improved conditions for rhodium catalyzed synthesis of sulfoximine (and sulfilimine) carbamates, especially for previously low-yielding carbamates containing π-functionality. Notably we report the preparation of propargyl sulfoximine carbamates to provide an alkyne as a potential click handle. Using Rh(2)(esp)(2) as catalyst and a DOE optimization approach provided considerably increased yields.
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spelling pubmed-97240922022-12-07 Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides Zhong, Zhenhao Chesti, Julian Armstrong, Alan Bull, James A. J Org Chem [Image: see text] Sulfoximines provide aza-analogues of sulfones, with potentially improved properties for medicinal chemistry. The sulfoximine nitrogen also provides an additional vector for the inclusion of other functionality. Here, we report improved conditions for rhodium catalyzed synthesis of sulfoximine (and sulfilimine) carbamates, especially for previously low-yielding carbamates containing π-functionality. Notably we report the preparation of propargyl sulfoximine carbamates to provide an alkyne as a potential click handle. Using Rh(2)(esp)(2) as catalyst and a DOE optimization approach provided considerably increased yields. American Chemical Society 2022-11-15 2022-12-02 /pmc/articles/PMC9724092/ /pubmed/36379008 http://dx.doi.org/10.1021/acs.joc.2c02083 Text en © 2022 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 Zhong, Zhenhao
Chesti, Julian
Armstrong, Alan
Bull, James A.
Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title_full Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title_fullStr Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title_full_unstemmed Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title_short Synthesis of Sulfoximine Propargyl Carbamates under Improved Conditions for Rhodium Catalyzed Carbamate Transfer to Sulfoxides
title_sort synthesis of sulfoximine propargyl carbamates under improved conditions for rhodium catalyzed carbamate transfer to sulfoxides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724092/
https://www.ncbi.nlm.nih.gov/pubmed/36379008
http://dx.doi.org/10.1021/acs.joc.2c02083
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