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Catalytic Asymmetric Addition of β-Ketoesters to Various Imines by Using Chiral Palladium Complexes

Authors

  • Yoshitaka Hamashima Dr.,

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • Naoki Sasamoto,

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • Daido Hotta,

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • Hidenori Somei Dr.,

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • Natsuko Umebayashi,

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • Mikiko Sodeoka Prof. Dr.

    1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Fax: (+81) 22-217-5601
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  • This work was supported in part by a Grant-in-Aid for Encouragement of Young Scientists (B) from JSPS. We thank Dr. T. Saito of Takasago International Corp. for providing the chiral phosphine ligands.

Abstract

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A highly enantioselective Mannich-type reaction of β-ketoesters was developed using a catalytic amount of the Pd–aqua complexes 1 (see scheme; PG=protecting group). A variety of imines derived from glyoxylate, as well as simple aromatic and α,β-unsaturated aldehydes were successfully used. The corresponding Mannich adducts were obtained in high yield with excellent enantioselectivity.

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