Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction

Abstract

The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of α-ketoamides with α,β-unsaturated aldehydes is described. The domino products were further derivatized by aldehyde olefination under one-pot conditions. The reaction proceeds with excellent diaste­reoselectivities (>20:1) and good to excellent enantioselectivities (60–96% ee).

Key words

organocatalysis - domino reactions - asymmetric synthesis - pyrrolidin-2-ones - aza-Michael addition

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