The synthesis of many drugs and natural products consists of the modification of N-alkenyl compounds. Nevertheless, their large structural variety and reactivity did not allow to find a general and stereoselective preparation method.
The research team of Petr Beier from IOCB Prague investigated the synthetic pathway leading to N-alkenyl derivatives using easily available N-fluoroalkyl-1,2,3-triazoles. The latter can be stereoselectively transformed in the presence of aluminum halide to bench-stable haloalkenyl imidoyl halides, and their further functionalization gives diverse and stereo-defined N-alkenyl products. A gram-scale synthesis and drug-analogs preparation demonstrated the robustness of the method.
Based on the computational studies, the authors have proposed the mechanism of the triazole ring-opening, which explains the stereoselective outcome of the reaction. The developed method offers new possibilities in synthetic chemistry using N-alkenyl derivatives.
Read the paper:
- Markos, A., Janecký, L., Chvojka, T., Martinek, T., Martinez‐Seara, H., Klepetářová, B. and Beier, P. (2021), Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N‐Alkenyl Compounds. Adv. Synth. Catal. https://doi.org/10.1002/adsc.202100009
