Tetrahydropyran‐Based Hybrid Dipeptides as Asymmetric Catalysts for Michael Addition of Aldehydes to β‐Nitrostyrenes

Abstract

AbstractA new series of hybrid dipeptide‐like organocatalysts based on pyranoid ϵ‐ or ζ‐amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to β‐nitrostyrenes. The reaction proceeds under mild conditions to afford a wide range of γ‐nitroaldehydes with up to 98% yield and up to 96% ee. These dipeptides are bifunctional organocatalysts, with a proline at the N‐terminus and a carboxylic acid at the C‐terminus. The tetrahydropyran unit embedded in the ϵ‐ or ζ‐amino acid induces a well‐defined conformation that is responsible for the catalysis. These dipeptides represent a new type of organocatalyst with a large number of possibilities to modulate their reactivity and selectivity.magnified image