Brion Aurélien, Martini Vittoria, Lombard Marine, Retailleau Pascal, Della Ca' Nicola, Neuville Luc, Masson Géraldine
Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
SynCat Lab, Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, 43124 Parma, Italy.
J Org Chem. 2024 Sep 6;89(17):12298-12306. doi: 10.1021/acs.joc.4c01239. Epub 2024 Aug 17.
Our study presents a novel enantioselective route for the synthesis of 1,2,3,4-tetrahydroquinolines via a chiral phosphoric acid-catalyzed three-component Povarov reaction, employing phenolic dienes as dienophiles. This approach produces a diverse array of 2,3,4-trisubstituted tetrahydroquinolines, each featuring a styryl group at position 4, in high yields with excellent regio-, diastereo-, and enantioselectivities (>95:5 dr and up to >99% ee).
