Brønsted Acid-Catalyzed Asymmetric Diels-Alder reactions of α,β-unsaturated Aldehydes and Cyclopentadiene

This master’s thesis details the Brønsted acid-catalyzed asymmetric Diels–Alder reaction between a variety of α,β-unsaturated aldehydes bearing different substitution patterns and dienes, in particular cyclopentadiene. Recent research efforts in our group using a one-pot multi-substrate screening methodological approach have shown that imidodiphosphorimidates (IDPis) are extremely potent catalysts for this transformation. Based on these results, we present the exploration of the aldehyde as well as the diene scope herein. Hence, a range of structurally distinct enals were initially prepared, and successfully utilized in subsequent catalysis experiments. To further demonstrate the robustness and scalability of the prior validated methodology, large scale experiments up to a multi-gram scale were conducted