Asymmetric Organocatalysis in the Remote (3 + 2)-Cycloaddition to 4-(Alk-1-en-1-yl)-3-cyanocoumarins
Beata Łukasik1, Marta Romaniszyn1, Nathan Kłoszewski1
1Institute of Organic Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
Abstract:
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.
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