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Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study

Authors

  • Yujiro Hayashi Prof. Dr.,

    1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Tsubasa Okano,

    1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Takahiko Itoh,

    1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Tatsuya Urushima,

    1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Hayato Ishikawa Dr.,

    1. Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601 (Japan), Fax: (+81) 3-5261-4631
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  • Tadafumi Uchimaru Dr.

    1. Research Institute for Computational Sciences, National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki 305-8568 (Japan)
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  • This work was partially supported by the Toray Science Foundation, and a Grant-in-Aid for Scientific Research from MEXT. We thank Tsukuba Advanced Computing Center (TACC) for the provision of computational facilities.

Abstract

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A chiral diaryl prolinol silyl ether organocatalyst with an acid is used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in good yields and with excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.

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