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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.

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Authors

James S. Sharley

Guido Gambacorta

Ana María Collado Pérez

Estela Espinos Ferri

Amadeo Fernandez Miranda

Jorge Sanchez Quesada



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.

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

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