Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals. Issue 41 (28th April 2022)

• Record Type: Journal Article
• Authors: Balletti, Matteo; Marcantonio, Enrico; Melchiorre, Paolo
• Is Part Of: Chemical communications. Volume 58:Issue 41(2022)
• Page Start: 6072
• Page End: 6075
• Publication Date: 2022-04-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc01638a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Reported herein is a rare example of asymmetric catalytic functionalisation of enals at the remote γ-position, proceeding via a radical path. 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 SN 2-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.