Activated Alkene Dependent One-Pot, Three-Component Aza-Morita−Baylis−Hillman Reaction of Ferrocenealdehyde: Synthesis of Highly Functionalized Diverse Ferrocene Derivatives

2011-04-01T00:00:00Z (GMT) by Suchithra Madhavan Ponnusamy Shanmugam
Activated alkene dependent one-pot, three-component aza-Morita−Baylis−Hillman (aza-MBH) reaction of ferrocenealdehyde afforded simple aza-MBH adduct of ferrocenealdehyde, unusual piperidine, β-amino acid residue, and γ-ketoester derivatives of ferrocene in good yield. The synthetic protocol with MVK has led to an unexpected ferrocenyl piperidine derivative in an excellent yield via diastereoselective domino aza-Michael/double Aldol pathway. Plausible mechanisms for the formation of unusual products and diastereoselectivity have also been described. The products can be used for the concise synthesis of ferrocenyl nitrogen heterocycles and bioconjugates.