Chiral Phosphoric Acid Catalyzed Inverse-Electron-Demand Aza-Diels-Alder Reaction of Isoeugenol Derivatives.

Long He , Mathieu Bekkaye , Pascal Retailleau (1) , Géraldine Masson (1)

1 ICSN - Institut de Chimie des Substances Naturelles

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).

Domaines: Chimie organique

Long He, Mathieu Bekkaye, Pascal Retailleau, Géraldine Masson. Chiral Phosphoric Acid Catalyzed Inverse-Electron-Demand Aza-Diels-Alder Reaction of Isoeugenol Derivatives.. Organic Letters, 2012, 14 (12), pp.3158-3161. ⟨10.1021/ol301251h⟩. ⟨hal-00722042⟩