Abstract:The optimized coupling of N-protected (S)-proline and (2S,4R)-4-hydroxyproline derivatives with (Z)-4-aminopent-3-en-2-one provided the expected β-ketoenamides in good to excellent yields. The subsequent intramolecular cyclizations afforded enantiopure pyridin-4-one derivatives with pyrrolidin-2-yl substituents. The nonaflates generated from these intermediates were excellent precursors for typical palladium-catalyzed coupling reactions. Oxidation with m-chloroperbenzoic acid gave pyrrolidine N-oxides whose su… Show more
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