Articles producció científica> Química Física i Inorgànica

Synthesis of Chiral, Fused Tricyclic Molecules by Sequential Metal-Catalyzed Reactions of Simple Substrates

  • Identification data

    Identifier: imarina:9283531
    Handle: https://hdl.handle.net/20.500.11797/imarina9283531
    Authors:
    Salto, JoanBiosca, MariaPamies, OscarDieguez, Montserrat
    Abstract:
    A set of complex tricyclic compounds containing several functional groups and multiple stereogenic centers has been prepared in only two steps with excellent diastereo- and enantioselectivities. The synthesis takes advantage of the highly versatile and enantioselective Pd-catalyzed allylic substitution of simple cyclic allylic acetates or carbonates to form chiral 1,6-, 1,7- and 1,8-enynes, which are then diastereoselectively transformed to the corresponding cyclopentenone- and cyclobutene-based tricyclic compounds.

  • Others:

    Author, as appears in the article.: Salto, Joan; Biosca, Maria; Pamies, Oscar; Dieguez, Montserrat
    Department: Química Física i Inorgànica
    URV's Author/s: Biosca Brull, Maria / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar / Saltó De La Torre, Joan
    Keywords: Tricarbocycles Sesquiterpene Pauson-khand reactions Pauson-khand Metal-catalysis Ligands Design Cyclizations Cobalt Asymmetric-synthesis Allylic substitution
    Abstract: A set of complex tricyclic compounds containing several functional groups and multiple stereogenic centers has been prepared in only two steps with excellent diastereo- and enantioselectivities. The synthesis takes advantage of the highly versatile and enantioselective Pd-catalyzed allylic substitution of simple cyclic allylic acetates or carbonates to form chiral 1,6-, 1,7- and 1,8-enynes, which are then diastereoselectively transformed to the corresponding cyclopentenone- and cyclobutene-based tricyclic compounds.
    Thematic Areas: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: maria.biosca@urv.cat joan.salto@estudiants.urv.cat joan.salto@estudiants.urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Author identifier: 0000-0002-9116-6318 0000-0003-4846-8473 0000-0003-4846-8473 0000-0002-2352-8508 0000-0002-8450-0656
    Record's date: 2025-01-27
    Paper version: info:eu-repo/semantics/publishedVersion
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Paper original source: Advanced Synthesis & Catalysis. 364 (21): 3682-3689
    APA: Salto, Joan; Biosca, Maria; Pamies, Oscar; Dieguez, Montserrat (2022). Synthesis of Chiral, Fused Tricyclic Molecules by Sequential Metal-Catalyzed Reactions of Simple Substrates. Advanced Synthesis & Catalysis, 364(21), 3682-3689. DOI: 10.1002/adsc.202200685
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2022
    Publication Type: Journal Publications

  • Keywords:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Tricarbocycles
    Sesquiterpene
    Pauson-khand reactions
    Pauson-khand
    Metal-catalysis
    Ligands
    Design
    Cyclizations
    Cobalt
    Asymmetric-synthesis
    Allylic substitution
    Química
    Organic chemistry
    Materiais
    Engenharias iv
    Engenharias ii
    Ciências biológicas ii
    Ciência de alimentos
    Chemistry, organic
    Chemistry, applied
    Catalysis
    Biodiversidade
    Astronomia / física

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