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Enantioselective Reaction of N-Unprotected Activated Ketimines with Phosphine Oxides Catalyzed by Chiral Imidazoline-Phosphoric Acids

Kazuki Ogura, Itsuki Isozumi, Tsunayoshi Takehara, Takeyuki Suzuki and Shuichi Nakamura*

*Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, Email:

K. Ogura, I. Isozumi, T. Takehara, T. Suzuki, S. Nakamura, Org. Lett., 2022, 24, 8088-8092.

DOI: 10.1021/acs.orglett.2c03457

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A bis(imidazoline)-phosphoric acid catalyzes an enantioselective hydrophosphonylation of ketimines with phosphine oxides to provide 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.

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Key Words

phosphine oxides, organocatalysis

ID: J54-Y2022