Highly diastereoselective synthesis of aza-diels-alder reaction of danishefsky diene wiht glyoxylate imines

Abstract

Aza-Diels-Alder reaction is an exceptionally powerful synthetic method for the construction of six-membered nitrogen-heterocycles.[1-3] The reaction of Danishefsky's diene 1 with iminoacetates 2 (imines of glyoxylates) provides a convenient protocol for the synthesis of pipiridone adducts 3 (Scheme 1). In this context, we have performed the synthesis of various cycloadducts, precursors of a wide variety of chiral piperidines with potential use as non-natural amino acids or as precursors of biologically active compounds, including iminosugars (glycomimetics).