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The Direct and Enantioselective, One-Pot, Three-Component, Cross-Mannich Reaction of Aldehydes

Yujiro Hayashi*, Wataru Tsuboi, Itaru Ashimine, Tatsuya Urushima, Mitsuru Shoji, Ken Sakai

*Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Email:

Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. Int. Ed., 2003, 42, 3677-3680.

DOI: 10.1002/anie.200351813


The one-pot, direct cross-Mannich reaction between two different aldehydes has been realized for the first time with high syn-diastereoselectivity and enantioselectivity by use of L-proline as organocatalyst. Side reactions, such as aldol condensation, can be suppressed at low reaction temperatures.

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Key Words

aldehydes, asymmetric synthesis, enantioselectivity, organocatalysis, Mannich Reaction, Multicomponent Reactions

ID: J06-Y2003-630