Issue 41, 2022

Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals

Abstract

Reported herein is a rare example of asymmetric catalytic functionalisation of enals at the remote γ-position, proceeding via a radical path. The process requires visible light and exploits the synergistic actions of two distinct organocatalysts. A nucleophilic organic catalyst generates radicals upon SN2-based activation of commercially available alkyl halides and blue light irradiation. Concomitantly, a chiral secondary amine catalyst triggers the formation of a dienamine from α-branched enals. This chiral dienamine intercepts the photogenerated radicals with excellent γ-selectivity and good stereocontrol.

Graphical abstract: Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals

Supplementary files

Article information

Article type
Communication
Submitted
22 mar 2022
Accepted
21 apr 2022
First published
21 apr 2022

Chem. Commun., 2022,58, 6072-6075

Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals

M. Balletti, E. Marcantonio and P. Melchiorre, Chem. Commun., 2022, 58, 6072 DOI: 10.1039/D2CC01638A

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