Light-Driven Enantioselective Organocatalytic β-Benzylation of Enals

Luca Dell'Amico, Victor M. Fernández-Alvarez, Feliu Maseras, Paolo Melchiorre

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34 Citations (Scopus)

Abstract

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Original languageEnglish
Pages (from-to)3304-3308
JournalAngewandte Chemie - International Edition
Volume56
Issue number12
DOIs
Publication statusPublished - 1 Jan 2017

Keywords

  • asymmetric catalysis
  • benzylation
  • organocatalysis
  • photochemistry
  • synthetic methods

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