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.

doi:10.1016/j.tet.2022.133058

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.

Authors

James S. Sharley

Guido Gambacorta

Ana María Collado Pérez

Estela Espinos Ferri

Amadeo Fernandez Miranda

Jorge Sanchez Quesada

Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor

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

Files

Published Journal Article (1.9 Mb)
PDF

Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

Copyright Statement
Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).