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

…, H Hussain, A Martel, A Kirschning, G Dujardin

Index: Gallier, Florian; Hussain, Hidayat; Martel, Arnaud; Kirschning, Andreas; Dujardin, Gilles Organic Letters, 2009 , vol. 11, # 14 p. 3060 - 3063

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Citation Number: 31

Abstract

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.