The application of organocatalytic bifunctional activation
in the
remote (3 + 2)-cycloaddition between 4-(alk-1-en-1-yl)-3-cyanocoumarins
and imines derived from salicylaldehyde is demonstrated. Products,
bearing two biologically relevant units, have been obtained with good
chemical and stereochemical efficiency. The stereochemical outcome
of the process results from the application of a quinine-derived catalyst.
Selected transformations of the cycloadducts leading to further chemical
diversity have been demonstrated.