Organocatalytic Asymmetric Michael Reaction of α,β-Unsaturated Imides

Significance

An organocatalytic asymmetric Michael reaction of activated methylene compounds with α,β-unsaturated imides has been described. Addition of soft nucleophiles 3 to imides 2 in the presence of 10 mol% of chiral thiourea 1 gives products of type 4 in high yields and enantio­selectivities. Subsequent treatment with hard nucleophiles 5 in a one-pot procedure furnishes the corresponding esters or amides 6 in good yields. Furthermore, mechanistic considerations based on NMR and IR spectroscopy, as well as kinetic studies are provided.