SYNTHESIS Best Paper Award 2022: Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Abstract

Background. Thieme Chemistry and the Editors of SYNTHESIS and SYNLETT present the 'SYNTHESIS/SYNLETT Best Paper Awards'. These annual awards honor the authors of the best original research papers in each of the journals, considering their immediate impact on the field of chemical synthesis. Professor Christoph Schneider, together with Fabian Hofmann, Cornelius Gärtner and Martin Kretzschmar from the University of Leipzig, Germany, are the recipients of the SYNTHESIS Best Paper Award 2022. The authors are recognized for their thorough examination of the title reaction. Mark Lautens, Editor-in-Chief of SYNTHESIS, stated: "The Schneider lab has reported on intramolecular aza-Diels-Alder reactions of ortho-quinone methide imines, giving access to biologically relevant tetrahydroquinolines. Key to their success was the use of chiral BINOL phosphoric amides as Bronsted acids. This comprehensive study presents successes and limitations, as well as proposes possible transition states to explain the results. The continuing importance of the Diels-Alder reaction, and its many variants, remains a topic of intense interest 70 years after the award of the Nobel Prize in Chemistry to Diels and Alder." SYNFORM spoke with Professor Christoph Schneider, who was happy to share some background information regarding the prize-winning paper as well as current research activities ongoing in his group.