Enantioselective Reaction of N-Unprotected Activated Ketimines with Phosphine Oxides Catalyzed by Chiral Imidazoline-Phosphoric Acids
K. Ogura, Itsuki Isozumi, Tsunayoshi Takehara, Takeyuki Suzuki, Shuichi Nakamura
Abstract
The first enantioselective hydrophosphonylation of ketimines with phosphine oxides was developed. The reaction of unprotected ketimines with phosphine oxides using a bis(imidazoline)-phosphoric acid catalyst gave chiral α-quaternary aminophosphorous compounds having a primary amino group in excellent yields and enantioselectivities. Based on experimental results and DFT calculation, transition states were proposed to explain the stereoselectivity of the reaction.
Topics & Concepts
ChemistryPhosphinePhosphoric acidEnantioselective synthesisCatalysisImidazoline receptorStereoselectivityOrganic chemistryMedicinal chemistryCombinatorial chemistryInternal medicineMedicineOrganophosphorus compounds synthesisAsymmetric Hydrogenation and CatalysisPhosphorus compounds and reactions