Chiral phosphoric acid catalyzed inverse-electron-demand aza-Diels-Alder reaction of isoeugenol derivatives.
Highly enantio- and diastereoselective three-component inverse electron-demand aza-Diels-Alder reaction of aldehydes, anilines, and isoeugenol derivatives catalyzed by a chiral phosphoric acid catalyst are reported. A wide variety of 2,3,4-trisubstituted tetrahydroquinolines containing an aryl group at the 4-position were obtained in a one-pot process with good to high yields and excellent stereoselectivities (>95:5 dr and up to >99% ee).
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, ICSN, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Long
L
He
Mathieu
M
Bekkaye
Pascal
P
Retailleau
Géraldine
G
Masson
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D005054:Eugenol / Q000031:analogs & derivatives* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
D001372:Aza Compounds; D007097:Imines; D010756:Phosphoric Acids; D005054:Eugenol; C036643:isoeugenol; C030242:phosphoric acid