We will present asymmetric Michael addition reactions of nitroalkane or dialkyl malonate to alpha,beta-unsaturated ketones by using helical-peptide foldamers as organocatalysts. A wide variety of alpha,beta-unsaturated ketones were examined, and the desired Michael addition products with high enantioselectivities (up to 99% ee) were obtained. An X-ray crystallographic analysis showed that the peptide foldamer catalyst formed a right-handed (<i>P</i>) alpha-helical structure. On the basis of these results and depsipeptide studies, the alpha-helical structures and the amide protons at the N-terminal region of peptide catalysts seemed to be crucial for the enantio-induction.

Asymmetric Michael addition reactions catalyzed by alpha,alpha-disubstituted alpha-amino acid-containing helical peptides

254th National Meeting (2017)

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