Issue 12, 2024

Ring expansion of unsubstituted aziridinium ylides to trifluoromethylated dehydropiperidines

Abstract

The first rhodium-catalyzed [3 + 3] ring expansion of unsubstituted aziridines was achieved using trifluoroalkenyl N-triftosylhydrazones as vinylcarbene precursors to afford a series of structurally diverse 2-trifluoromethylated dehydropiperidines under mild conditions. DFT calculations supported a scheme involving aziridinium ylide formation followed by a [1,4] sigmatropic rearrangement sequence. Notably, the reaction shows broad scope and functional group tolerance, which enables the translation of routine olefination of unsubstituted aziridinium ylides into a strategy for heterocyclic ring syntheses. Beyond enabling access to valuable dehydropiperidines from easily prepared starting materials, we also demonstrated the synthetic utility of this approach in the late-stage modification of bioactive compounds.

Graphical abstract: Ring expansion of unsubstituted aziridinium ylides to trifluoromethylated dehydropiperidines

Supplementary files

Article information

Article type
Research Article
Submitted
23 Mar 2024
Accepted
22 Apr 2024
First published
24 Apr 2024

Org. Chem. Front., 2024,11, 3358-3363

Ring expansion of unsubstituted aziridinium ylides to trifluoromethylated dehydropiperidines

J. Tang, T. Tian, Y. Wang, D. Wei, Y. Yang, X. Wang, P. Sivaguru, Y. Ning, Z. Liu and V. Nenajdenko, Org. Chem. Front., 2024, 11, 3358 DOI: 10.1039/D4QO00537F

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