Enantioselective Formal ?-Methylation and ?-Benzylation of Aldehydes by Means of Photo-organocatalysis.

ABSTRACT: Detailed herein is the photochemical organocatalytic enantioselective ?-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.

SUBMITTER: Filippini G 

PROVIDER: S-EPMC5396335 | biostudies-other | 2017 Apr

REPOSITORIES: biostudies-other