Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems

[Image: see text] Herein, we report a new application of β-nitroenones as valuable building blocks for the preparation of polyfunctionalized homoallylic alcohols; they can be used as key precursors of conjugated nitrotriene systems. The synthesis of homoallylic alcohols was performed exploiting the...

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Autores principales: Yuan, Lixia, Kachalova, Liudmila, Khan, Muhammad E. I., Ballini, Roberto, Petrini, Marino, Palmieri, Alessandro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088019/
https://www.ncbi.nlm.nih.gov/pubmed/36926909
http://dx.doi.org/10.1021/acs.joc.2c02669
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author Yuan, Lixia
Kachalova, Liudmila
Khan, Muhammad E. I.
Ballini, Roberto
Petrini, Marino
Palmieri, Alessandro
author_facet Yuan, Lixia
Kachalova, Liudmila
Khan, Muhammad E. I.
Ballini, Roberto
Petrini, Marino
Palmieri, Alessandro
author_sort Yuan, Lixia
collection PubMed
description [Image: see text] Herein, we report a new application of β-nitroenones as valuable building blocks for the preparation of polyfunctionalized homoallylic alcohols; they can be used as key precursors of conjugated nitrotriene systems. The synthesis of homoallylic alcohols was performed exploiting the chemoselective addition of metal allylating agents to the ketone moiety vs the nitroalkenyl group. The conversion of alcohols into nitrotrienes was achieved under Lewis-acid-promoted conditions. Both classes of compounds were obtained in good to excellent yields.
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spelling pubmed-100880192023-04-12 Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems Yuan, Lixia Kachalova, Liudmila Khan, Muhammad E. I. Ballini, Roberto Petrini, Marino Palmieri, Alessandro J Org Chem [Image: see text] Herein, we report a new application of β-nitroenones as valuable building blocks for the preparation of polyfunctionalized homoallylic alcohols; they can be used as key precursors of conjugated nitrotriene systems. The synthesis of homoallylic alcohols was performed exploiting the chemoselective addition of metal allylating agents to the ketone moiety vs the nitroalkenyl group. The conversion of alcohols into nitrotrienes was achieved under Lewis-acid-promoted conditions. Both classes of compounds were obtained in good to excellent yields. American Chemical Society 2023-03-16 /pmc/articles/PMC10088019/ /pubmed/36926909 http://dx.doi.org/10.1021/acs.joc.2c02669 Text en © 2023 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 Yuan, Lixia
Kachalova, Liudmila
Khan, Muhammad E. I.
Ballini, Roberto
Petrini, Marino
Palmieri, Alessandro
Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title_full Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title_fullStr Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title_full_unstemmed Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title_short Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems
title_sort overcoming the usual reactivity of β-nitroenones: synthesis of polyfunctionalized homoallylic alcohols and conjugated nitrotriene systems
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088019/
https://www.ncbi.nlm.nih.gov/pubmed/36926909
http://dx.doi.org/10.1021/acs.joc.2c02669
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