biostudies-literatureFilippini GAgència de Gestió d’Ajuts Universitaris i de RecercaEuropean Research CouncilMineco4447-4451https://www.ebi.ac.uk/biostudies/studies/S-EPMC5396335biostudies-literatureUnknown56(16)Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.Angewandte Chemie (International ed. in English)Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis.PMC5396335681840SEV-2013-03192014 SGR 1059Melchiorre PFilippini GSilvi MfalseEnantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis.Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.2017-01-01T00:00:00Z2017 Apr2025-04-26T18:48:50.559Z2019-03-27T02:41:34ZS-EPMC53963352832336710.1002/anie.201612045