Enantioselective Formal α‐Methylation and α‐Benzylation of Aldehydes by Means of Photo‐organocatalysis
Open Access
- 21 March 2017
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 56 (16), 4447-4451
- https://doi.org/10.1002/anie.201612045
Abstract
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.Keywords
Funding Information
- European Research Council (681840)
- Agència de Gestió d’Ajuts Universitaris i de Recerca (2014 SGR 1059)
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