Hetero-Diels-Alder Reactions of Cyclic Ketone Derived Enamide. A New and Efficient Concept for the Asymmetric Robinson Annulation

Florian Gallier (1) , Hidayat Hussain (1) , Arnaud Martel (1) , Andreas Kirschning (1) , Gilles Dujardin (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire

Chiral enamides, easily prepared in one step from a cyclic ketone and an oxazolidinone, are successfully employed in high-yielding, endo, and facially selective Hetero-Diels−Alder reactions involving activated oxadienes and Siever’s reagent as catalyst. From the resulting bicyclic heteroadducts, a novel and efficient asymmetric modification for the Robinson annulation of cyclic monoketones is described.

Domaines: Chimie organique

Florian Gallier, Hidayat Hussain, Arnaud Martel, Andreas Kirschning, Gilles Dujardin. Hetero-Diels-Alder Reactions of Cyclic Ketone Derived Enamide. A New and Efficient Concept for the Asymmetric Robinson Annulation. Organic Letters, 2009, 11 (14), pp.3060-3063. ⟨10.1021/ol901065e⟩. ⟨hal-00414358⟩