Chemoselectivity

Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters

Rebecca Hermans, Max Van Hoof, Luc Van Meervelt & Wim Dehaen · Organics · 2023

The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles a...

Open access Research Article 10.3390/org4020012

Theoretical Insight into the Reversal of Chemoselectivity in Diels-Alder Reactions of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Brønsted and Lewis Acids

Lakhdar Benhamed, Sidi Mohamed Mekelleche & Wafaa Benchouk · Organics · 2021

Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reac...

Open access Research Article 10.3390/org2010004