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

Beilstein J Org Chem. 2012:8:1452-7. doi: 10.3762/bjoc.8.165. Epub 2012 Sep 4.

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.