Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones

Abstract

The organocatalytic Michael addition of malonates to symmetric unsaturated 1,4-diketones catalyzed by thiourea and squaramide derivatives with Cinchona alkaloids afforded the formation of a new C–C bond in high yields (up to 98%) and enantiomeric purities (up to 93%). The absolute configuration of the product was suggested from comparison of the experimental and calculated VCD spectra of the reaction product 3a.

Keywords

• Michael addition
• non-covalent catalysis
• organocatalysis
• squaramide
• thiourea