Organocatalytic Approaches towards the Synthesis of Asymmetric Tetrahydroquinoline (THQ) Derivatives

Among the N-heterocyclic compounds, the delightful 1,2,3,4-tetrahydroquinolines (THQs) shine brightly due to their abundant presence in molecules of significant biological importance and pharmaceuticals with diverse biological activities. Charming derivatives like angustureine and cuspareine spring from the Galipea officinalis, while the captivating martinelline and martinellic acid are treasures from Martinella iquitosenses. The allure of THQs lies in their vast biological potential and the intriguing challenge of natural isolation. To capture these gems, various synthetic routes have been crafted, such as the hydrogenation of quinolines, domino reactions, intramolecular cyclization, and notably, the ingenious Povarov reaction. As the 21st century dawned, a new star ascended in the realm of asymmetric synthesis: organocatalysis. celebrated as the "third pillar" alongside metal catalysts and biocatalysts, organocatalysis employs small, chiral organic molecules to gracefully orchestrate organic transformations under gentle conditions. This approach not only offers remarkable efficiency but also crafts complex molecular structures with high precision. Its simplicity and the accessibility of catalytic systems have made organocatalysis a beloved method, ensuring high yields and exceptional enantiomeric excess across a myriad of organic reactions.

Publication History

Received: 31 May 2024

Accepted after revision: 30 July 2024

Accepted Manuscript online:
30 July 2024