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
Read the publication that featured this abstractConversion 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.
Get in touch
For more information on flow chemistry systems and services please use the contact methods below.
Call us on +44 (0)1284 728659 or Email us
Resource Centre
R-Series

The Vapourtec R-Series is, quite simply, unrivalled for flow chemistry
- Flexible |
- Precise |
- Automatable
The R-Series is undoubtedly the most versatile, modular flow chemistry system available today.
E-Series

The Vapourtec E-Series is the perfect introductory system for flow chemistry
- Robust |
- Easy to use |
- Affordable
The E-Series is a robust and affordable, entry level flow chemistry system designed for reliability and ease of use.