Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights

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  • ChemInform Abstract: Helical‐Peptide‐Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights.

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Helical peptide foldamer catalyzed Michaeladdition reactions of nitroalkane or dialkyl malonate toα,β-unsaturated ketones are reported along with the mechanisticconsiderations of the enantio-induction. A wide variety ofα,β-unsaturated ketones, includingβ-aryl,β-alkyl enones, andcyclic enones, were found to be catalyzed by the helical peptideto give Michael adducts with high enantioselectivities (up to99%). On the basis of X-ray crystallographic analysis anddepsipeptide study, the amide protons, N(2)−H and N(3)−H,at the N terminus in theα-helical peptide catalyst were crucialfor activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminiumion intermediates.

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