American Chemical Society
ol301251h_si_001.cif (20.54 kB)

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

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posted on 2016-02-20, 19:25 authored by Long He, Mathieu Bekkaye, Pascal Retailleau, Géraldine Masson
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).