An efficient and enantioselective Michael addition of aromatic oximes to α,β‐unsaturated aldehydes promoted by a chiral diamine catalyst derived from α,α‐diphenyl prolinol

Abstract

Chiral diamine catalysts 11a-e derived from α,α-diphenyl prolinol were prepared and successfully applied to the Michael addition of aromatic oximes to α,β-unsaturated aldehydes in mediocre to good yields (up to 78%) and good to high enantioselectivities (up to 93% ee).

Theoretical study on the reaction mechanisms of Michael chirality addition between propionaldehyde and nitroalkene catalyzed by an enantioselective catalyst

“…In recent years, many chemists are committed in overcoming the synthetic challenges. The stereoselectivity syntheses can be divided into two categories according to their origin: inspiration from the nature or coming from the wisdom of human . Approximately 60% of all pharmaceutical agents currently on the market are chiral medicament, and for the intended biological target, the development of enantiomerically pure formulations is often critical to ensure high specificity .…”

“…The stereoselectivity syntheses can be divided into two categories according to their origin: inspiration from the nature or coming from the wisdom of human. 1,2 Approximately 60% of all pharmaceutical agents currently on the market are chiral medicament, and for the intended biological target, the development of enantiomerically pure formulations is often critical to ensure high specificity. 3 An important endeavor in the field of developing of a new effective chiral ligand and catalyst, which exhibits the high stereoselectivity and enantioselectivity with novel skeletons, continues to be a challenging goal for organic chemists.…”