Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene–Ene–Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism

Daniel Cassú, Teodor Parella, Miquel Solà, Anna Pla-Quintana, Anna Roglans

    Research output: Contribution to journalArticleResearchpeer-review

    11 Citations (Scopus)

    Abstract

    © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Allene-(E)-ene-yne N-tosyl-tethered substrates 3 a–3 h were efficiently prepared and their rhodium-catalyzed [2+2+2] cycloaddition reactions were evaluated. The cycloadditions are chemoselective as only the proximal double bond of the allene reacted to afford exocyclic double bonds in the fused-tricyclic scaffolds. The stereoselectivity depended on the catalytic system used. Reactivity between allene, alkene, and alkyne was studied for the first time by density functional theory calculations. This mechanistic study determines the order in which the unsaturated groups take part in the catalytic cycle.
    Original languageEnglish
    Pages (from-to)14889-14899
    JournalChemistry - A European Journal
    Volume23
    Issue number59
    DOIs
    Publication statusPublished - 20 Oct 2017

    Keywords

    • allenes
    • cycloaddition
    • density functional calculations
    • reaction mechanisms
    • rhodium

    Fingerprint Dive into the research topics of 'Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene–Ene–Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism'. Together they form a unique fingerprint.

  • Cite this

    Cassú, D., Parella, T., Solà, M., Pla-Quintana, A., & Roglans, A. (2017). Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene–Ene–Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism. Chemistry - A European Journal, 23(59), 14889-14899. https://doi.org/10.1002/chem.201703194