Alkynes to (Free) Carbenes to Polycyclic Cyclopropanes

Alexander L. Guzman, Alexis N. Mann, Thomas R. Hoye

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Carbenes and carbenoids are commonly employed for the synthesis of cyclopropane-containing compounds. Here we report the metal-free, intramolecular cyclopropanation of tethered alkenes by free carbenes derived from alkynes to construct structurally unique multicyclic cyclopropanes with perfect atom economy. The nature of the tether influences both the rate of carbene formation and subsequent competing reaction events. Some of the substrates lead to metastable cyclopropane intermediates that further fragment to furnish interesting isomeric products by mechanistically novel processes. A removable siloxane tether can be utilized to achieve formal intermolecular cyclopropanations and to access cyclopropanol derivatives.

    Original languageEnglish (US)
    Pages (from-to)28642-28647
    Number of pages6
    JournalJournal of the American Chemical Society
    Volume146
    Issue number42
    DOIs
    StatePublished - Oct 23 2024

    Bibliographical note

    Publisher Copyright:
    © 2024 American Chemical Society.

    PubMed: MeSH publication types

    • Journal Article

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