Interrupted Curtius Rearrangements of Quaternary Proline Derivatives: A Flow Route to Acyclic Ketones and Unsaturated Pyrrolidines

    • Marcus Baumanna
    • Thomas S. Moodyb, c
    • Megan Smythb
    • Scott Wharryb
    • aSchool of Chemistry, University College Dublin, Science Centre South, Belfield D04 N2E2, Ireland
    • bDepartment of Technology, Almac Sciences, 20 Seagoe Industrial Estate, Craigavon BT63 5QD, United Kingdom
    • cArran Chemical Company, Roscommon N37 DN24, Ireland

    Conversion of N-Boc-protected quaternary proline derivatives under thermal Curtius rearrangement conditions was found to afford a series of ring-opened ketone and unsaturated pyrrolidine products instead of the expected carbamate species. The nature of the substituent on the quaternary carbon thereby governs the product outcome due to the stability of a postulated N-acyliminium species. A continuous flow process with in-line scavenging was furthermore developed to streamline this transformation and safely create products on a gram scale.

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