Highly Efficient Dynamic Kinetic Resolution of Azlactones by Urea-Based Bifunctional Organocatalysts


  • This work was supported by the Fonds der Chemischen Industrie, in particular through a doctoral fellowship to F.C. The authors thank Degussa AG, Hanau for generous gifts of amino acids. Samples of compounds 2 and 1013 were kindly provided by Katrin Roland, Burkhard Koch, Marc Brandenburg, and Stefan Schnippering.


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Novel tasks for a venerable molecule: Bifunctional organocatalysts of the type shown, with a quasi Lewis acidic urea or thiourea unit and a Brønsted basic amine functionality, effect the dynamic kinetic resolution of azlactones with high enantioselectivity. N-Benzoyl amino acid esters were obtained with up to 91 % ee in high yields from racemic azlactones.