Further investigations into imine-mediated formation of allylic nitro compounds

Sharley, James S.; Gambacorta, Guido; Collado Pérez, Ana María; Ferri, Estela Espinos; Miranda, Amadeo Fernandez; Quesada, Jorge Sanchez; Baxendale, Ian R.

Abstract

Nitro alkanes are valuable starting materials for functionalisation via their corresponding anions as well as their transformation into other important groups such as ketones via the Nef reaction. Herein, we report a process development study for the construction of a series of cyclic allylic nitro compounds that features a greener solvent and a lower cost, more robust catalyst than previously reported. The process was developed to target the selective synthesis of an important fragrance intermediate, namely, α-dehydroherbac. Process scoping and optimisation involved solvent & catalyst screening along with a basic kinetic investigation to evaluate critical reaction parameters (concentration and reagents ratio). The final optimised conditions were further demonstrated via synthesis of a small collection of additional derivatives to demonstrate scope and utility.

Citation

Sharley, J. S., Gambacorta, G., Collado Pérez, A. M., Ferri, E. E., Miranda, A. F., Quesada, J. S., & Baxendale, I. R. (2022). Further investigations into imine-mediated formation of allylic nitro compounds. Tetrahedron, 126, https://doi.org/10.1016/j.tet.2022.133058

• Journal Article Type: Article
• Acceptance Date: Sep 22, 2022
• Online Publication Date: Oct 23, 2022
• Publication Date: 2022
• Deposit Date: Nov 21, 2022
• Publicly Available Date: Nov 21, 2022
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 126
• DOI: https://doi.org/10.1016/j.tet.2022.133058
• Public URL: https://durham-repository.worktribe.com/output/1185745