33738-54-4Relevant academic research and scientific papers
Light-Driven Enantioselective Organocatalytic β-Benzylation of Enals
Dell'Amico, Luca,Fernández-Alvarez, Victor M.,Maseras, Feliu,Melchiorre, Paolo
, p. 3304 - 3308 (2017)
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.
