Combining Iminium and Supramolecular Catalysis for the [4 + 2] Cycloaddition of E-Cinnamaldehydes

07 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein we describe a method for combining supramolecular catalysis with imininum-based organocatalysis in the Diels–Alder cycloaddition reaction. Notably, both cage and L-proline are required for the reaction to occur, implying that encap-sulation of the substrates and co-catalyst are necessary for the reaction to occur. We explore the substrate scope for a va-riety of E-cinnamaldehydes and dienes. Finally, we probe the supramolecular assembly processes responsible for the observed catalysis using NMR spectroscopic methods, determining that the reaction is negative order in the cinnamalde-hyde substrate and experiences product inhibition.

Keywords

Organocatalysis
Supramolecular Catalysis
Resorcinarene Hexamer
Diels–Alder Reaction

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.