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 Marts 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements