Synthesis of novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions

A new type of phosphate-pyridine (P, N) ligand derived from d-glucosamine and BINOL was synthesized and successfully applied in Cu-catalyzed enantioselective conjugate addition of diethylzinc to chalcones for the first time, high yields and enantioselectivities were obtained when the ligand 10a which contains (S)-BINOL was used. The results also showed that the configuration of BINOL at the ligand backbone had remarkable effects on the activities and enantioselectivities.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A new type of P,N ligand which derived from D-glucosamine was synthesized. ► It has been successfully used in asymmetric 1,4-conjugate addition reactions. ► The configuration of BINOL at the ligand have effect on the reaction was proved.