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Keywords:

  • amides;
  • asymmetric catalysis;
  • butenolides;
  • Michael addition;
  • vinylogous conjugate addition
Thumbnail image of graphical abstract

The strength of the weak: An L-tert-leucine-derived amine–thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state.