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
Balletti, M., Marcantonio, E., Melchiorre, P. (2022). Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals. CHEMICAL COMMUNICATIONS, 58(41), 6072-6075 [10.1039/D2CC01638A].
Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals
Melchiorre, Paolo
Ultimo
Supervision
2022
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 stereocontrolFile | Dimensione | Formato | |
---|---|---|---|
Chem. Commun. 58, 6072–6075.pdf
Open Access dal 23/03/2023
Tipo:
Postprint
Licenza:
Licenza per Accesso Aperto. Altra tipologia di licenza compatibile con Open Access
Dimensione
1.38 MB
Formato
Adobe PDF
|
1.38 MB | Adobe PDF | Visualizza/Apri |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.