Enantioselective catalysis of the intermolecular [2+2] photocycloaddition between 2-pyridones and acetylenedicarboxylates

Mark M. Maturi, Thorsten Bach

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114 Scopus citations


Intermolecular [2+2] photocycloadditions represent the most versatile and widely applicable of photochemical reactions. For the first time, such intermolecular reactions have been carried out in a catalytic fashion using a chiral triplet sensitizer, with high enantioselectivity (up to 92 % ee). The low catalyst loading (2.5-5 mol %) underlines the high efficiency of the process both in terms of reaction acceleration and differentiation of the enantiotopic faces of the substrate. The substrate is anchored to the chiral catalyst through noncovalent interactions (hydrogen bonds), thus providing a chiral environment in which the enantioselective photocycloaddition proceeds. The densely functionalized products present numerous possibilities for further synthetic transformations.

Original languageEnglish
Pages (from-to)7661-7664
Number of pages4
JournalAngewandte Chemie International Edition in English
Issue number29
StatePublished - 14 Jul 2014


  • cycloaddition
  • enantioselectivity
  • hydrogen bonds
  • organocatalysis
  • photochemistry
  • sensitizers


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