1246524-25-3Relevant academic research and scientific papers
Combined organo- and gold-catalyzed enantioselective synthesis of bicyclic enones
Zweifel, Theo,Hollmann, Dirk,Prueger, Birgit,Nielsen, Martin,Jorgensen, Karl Anker
experimental part, p. 1624 - 1629 (2010/11/04)
By combining organocatalysis with gold catalysis highly enantioenriched bicyclic enones are available via an operationally simple one-pot procedure. Iminium-ion activation by cinchona alkaloid-derived primary amine catalysts induces the Michael addition of propargylated malononitriles and cyanoacetates to α,β-unsaturated ketones. The resulting intermediates undergo an exo-dig cyclization, forming a new C-C bond followed by double-bond isomerization to give highly functionalized bicyclic enones in good yields and high enantioselectivities.
