The lipase-catalyzed asymmetric C–C Michael addition

The example of enzyme-catalyzed asymmetric C–C Michael addition was observed using Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus) in organic medium in the presence of water. This biocatalysis is applicable to the Michael additions of a wide range of 1,3-dicarbonyl compounds and cyclohexanone to aromatic and heteroaromatic nitroolefins and cyclohexenone. The enantioselectivities up to 83% ee and yields up to 90% were achieved. The enzyme can be reused for three cycles.

Graphical abstractThe example of enzyme-catalyzed asymmetric Michael addition was observed using Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus) in organic medium in the presence of water. This biocatalysis is applicable to the Michael additions of a wide range of 1,3-dicarbonyl compounds and cyclohexanone to aromatic and heteroaromatic nitroolefins and cyclohexenone. The enantioselectivities up to 83% ee and yields up to 90% were achieved. The enzyme can be reused for three cycles.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights▶ The enzyme-catalyzed asymmetric C–C Michael addition was observed. ▶ Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus) was used in DMSO/H2O. ▶ The enantioselectivities up to 83% ee and yields up to 90% were achieved. ▶ The enzyme can be reused for three cycles.