Enantioselective Formal a-Methylation and a-Benzylation of Aldehydes by Means of Photo-organocatalysis
Detailed herein is the photochemical organocatalytic enantioselective a-alkylation of aldehydes with (phenylsulfo- nyl)alkyl iodides. The chemistry relies on the direct photo- excitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground- st...
| Autores: | , , |
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| Tipo de documento: | artigo |
| Estado: | Versión aceptada para publicación |
| Data de publicação: | 2017 |
| País: | España |
| Recursos: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositório: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/350688 |
| Acesso em linha: | http://hdl.handle.net/2072/350688 https://doi.org/10.1002/anie.201612045 |
| Access Level: | Acceso aberto |
| Palavra-chave: | 54 |
| Resumo: | Detailed herein is the photochemical organocatalytic enantioselective a-alkylation of aldehydes with (phenylsulfo- nyl)alkyl iodides. The chemistry relies on the direct photo- excitation 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. |
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