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

Lixia Yuan, Liudmila Kachalova, Muhammad E I Khan, Roberto Ballini, Marino Petrini, Alessandro Palmieri

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Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Lixia YuanGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.

Liudmila KachalovaGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.

Muhammad E I KhanGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.

Roberto BalliniGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.ORCID 0000-0002-5107-6449

Marino PetriniGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.ORCID 0000-0002-4941-5878

Alessandro PalmieriGreen Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.ORCID 0000-0001-6599-3937

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

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.

Identifiers

PMID36926909

DOI10.1021/acs.joc.2c02669

PMCPMC10088019

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