Combining iminium and supramolecular catalysis for the [4 + 2] cycloaddition of -cinnamaldehydes.

Org Biomol Chem

Department of Chemistry & Biochemistry, School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft St., Mailstop 602, Toledo, OH 43606, USA.

Published: August 2022

Herein we describe a method for combining supramolecular catalysis with imininum-based organocatalysis in the Diels-Alder cycloaddition reaction. Both supramolecular host and L-proline are required for the reaction to occur, implying that encapsulation of the substrates and co-catalyst are necessary for the reaction to occur. We explore the substrate scope for a variety of -cinnamaldehydes and dienes. Finally, we probe the supramolecular assembly processes responsible for the observed catalysis using NMR spectroscopic methods.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462845PMC
http://dx.doi.org/10.1039/d2ob01171aDOI Listing

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