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Direct Asymmetric Mannich-Type Reaction of α-Isocyanoacetates with Ketimines using Cinchona Alkaloid/Copper(II) Catalysts


  • This work was partially supported by Grants-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts” from MEXT (26105727) and the Nagase Science Technology Foundation. M.H. thanks JSPS for research fellowships. We thank Prof. Norio Shibata at Nagoya Institute of Technology for unrestricted access to analytical facilities.


The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.