Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions

[Image: see text] 1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence of electrophiles, was investigated. This strategy led to the synthesis of new, stable N-protected isoxazol-5-ones in good yields and hig...

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Autores principales: Macchia, Antonio, Summa, Francesco F., Monaco, Guglielmo, Eitzinger, Andreas, Ofial, Armin R., Di Mola, Antonia, Massa, Antonio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8928520/
https://www.ncbi.nlm.nih.gov/pubmed/35309475
http://dx.doi.org/10.1021/acsomega.1c07081
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author Macchia, Antonio
Summa, Francesco F.
Monaco, Guglielmo
Eitzinger, Andreas
Ofial, Armin R.
Di Mola, Antonia
Massa, Antonio
author_facet Macchia, Antonio
Summa, Francesco F.
Monaco, Guglielmo
Eitzinger, Andreas
Ofial, Armin R.
Di Mola, Antonia
Massa, Antonio
author_sort Macchia, Antonio
collection PubMed
description [Image: see text] 1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence of electrophiles, was investigated. This strategy led to the synthesis of new, stable N-protected isoxazol-5-ones in good yields and high diastereolectivity. The study of the reactivity of obtained products in the presence of the Mo(CO)(6)/H(2)O system allowed the development of a cascade reaction leading to novel methyl ketones in high yields and unchanged dr bearing an uncommon chloromethinearylsulfonyl end group.
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spelling pubmed-89285202022-03-18 Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions Macchia, Antonio Summa, Francesco F. Monaco, Guglielmo Eitzinger, Andreas Ofial, Armin R. Di Mola, Antonia Massa, Antonio ACS Omega [Image: see text] 1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence of electrophiles, was investigated. This strategy led to the synthesis of new, stable N-protected isoxazol-5-ones in good yields and high diastereolectivity. The study of the reactivity of obtained products in the presence of the Mo(CO)(6)/H(2)O system allowed the development of a cascade reaction leading to novel methyl ketones in high yields and unchanged dr bearing an uncommon chloromethinearylsulfonyl end group. American Chemical Society 2022-03-04 /pmc/articles/PMC8928520/ /pubmed/35309475 http://dx.doi.org/10.1021/acsomega.1c07081 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 Macchia, Antonio
Summa, Francesco F.
Monaco, Guglielmo
Eitzinger, Andreas
Ofial, Armin R.
Di Mola, Antonia
Massa, Antonio
Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title_full Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title_fullStr Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title_full_unstemmed Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title_short Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)(6)-Mediated Reductive Cascade Reactions
title_sort access to β-alkylated γ-functionalized ketones via conjugate additions to arylideneisoxazol-5-ones and mo(co)(6)-mediated reductive cascade reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8928520/
https://www.ncbi.nlm.nih.gov/pubmed/35309475
http://dx.doi.org/10.1021/acsomega.1c07081
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