Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization

[Image: see text] A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Pr...

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Autores principales: Carballo, Rubén M., Padrón, José M., Fernández, Israel, Cruz, Daniel A., Grmuša, Luana, Martín, Víctor S., Padrón, Juan I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396664/
https://www.ncbi.nlm.nih.gov/pubmed/35921221
http://dx.doi.org/10.1021/acs.joc.2c01267
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author Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
author_facet Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
author_sort Carballo, Rubén M.
collection PubMed
description [Image: see text] A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative activity for this family of sulfonyl amides is also included.
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spelling pubmed-93966642022-08-24 Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization Carballo, Rubén M. Padrón, José M. Fernández, Israel Cruz, Daniel A. Grmuša, Luana Martín, Víctor S. Padrón, Juan I. J Org Chem [Image: see text] A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative activity for this family of sulfonyl amides is also included. American Chemical Society 2022-08-03 2022-08-19 /pmc/articles/PMC9396664/ /pubmed/35921221 http://dx.doi.org/10.1021/acs.joc.2c01267 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 Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_full Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_fullStr Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_full_unstemmed Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_short Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_sort iron(iii)-catalyzed synthesis of 2-alkyl homoallyl sulfonyl amides: antiproliferative study and reactivity scope of aza-prins cyclization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396664/
https://www.ncbi.nlm.nih.gov/pubmed/35921221
http://dx.doi.org/10.1021/acs.joc.2c01267
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