Visible Light-Mediated Decarboxylation Rearrangement Cascade of ω-Aryl- N-(acyloxy)phthalimides

The Journal of Organic Chemistry
Christian FaderlOliver Reiser

Abstract

A Smiles-type radical rearrangement induced by visible-light-mediated decarboxylation of ω-aryl- N-(acyloxy)phthalimides was developed, giving rise to pharmacologically important substance classes: phenylethylamine derivatives, dihydroisoquinolinones, and benzoazepinones were synthesized on the basis of readily available benzoic acids or benzaldehydes and β- or γ-amino acids. This methodology facilitates the synthesis of enantiopure D-amphetamine and of precursors of capsazepinoid bronchodilators.

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Citations

Aug 29, 2020·Chemical Communications : Chem Comm·David M WhalleyMichael F Greaney
Oct 1, 2020·Chemistry : a European Journal·Marie HuynhEtienne Brachet
May 29, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Diego Francisco Chicas-Baños, Bernardo A Frontana-Uribe
Aug 14, 2021·Chemical Reviews·Xue-Qiang ChuChao-Jun Li
Jun 27, 2020·The Journal of Organic Chemistry·José Tiago M CorreiaMárcio W Paixão
Jan 14, 2020·Journal of the American Chemical Society·Martins S OderindeT G Murali Dhar

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