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- Title
Light-Driven Enantioselective Organocatalytic β-Benzylation of Enals.
- Authors
Dell'Amico, Luca; Fernández-Alvarez, Victor M.; Maseras, Feliu; Melchiorre, Paolo
- Abstract
A photochemical organocatalytic strategy for the direct enantioselective β-benzylation of α,β-unsaturated aldehydes is reported. The chemistry capitalizes upon the light-triggered enolization of 2-alkyl-benzophenones to afford hydroxy- o-quinodinomethanes. These fleeting intermediates are stereoselectively intercepted by chiral iminium ions, transiently formed upon condensation of a secondary amine catalyst with enals. Density functional theory (DFT) studies provided an explanation for why the reaction proceeds through an unconventional Michael-type addition manifold, instead of a classical cycloaddition mechanism and subsequent ring-opening.
- Subjects
PHOTOCHEMICAL oxidants; ORGANOCATALYSIS; DENSITY functional theory; CARBOCYCLIC compounds; RING formation (Chemistry)
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 12, p3304
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201612159