l-Prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins

Though many chiral amines such as l-proline and its derivatives have proven to be versatile catalysts in many reactions, l-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first l-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13–>99:1) and enantioselectivities (82–96%).

Graphical abstractThe first l-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13–>99:1) and enantioselectivities (82–96%) was described.Figure optionsDownload full-size imageDownload as PowerPoint slide