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Chiral Silver Amide Catalyst for the [3+2] Cycloaddition of α-Amino Esters to Olefins

Authors

  • Dr. Yasuhiro Yamashita,

    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033 (Japan), Fax: (+81) 3-5684-0634
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  • Takaki Imaizumi,

    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033 (Japan), Fax: (+81) 3-5684-0634
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  • Prof. Dr. Shū Kobayashi

    Corresponding author
    1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033 (Japan), Fax: (+81) 3-5684-0634
    • Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033 (Japan), Fax: (+81) 3-5684-0634
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  • This work was partially supported by a Grant-in-Aid for Science Research from the Japan Society for the Promotion of Science (JSPS), the Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering), the University of Tokyo, and theMEXT (Japan). We thank Takasago Int. Co. for supply of (R)-DTBM-segphos.

Abstract

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Silberstreif: Eine hoch exo-selektive asymmetrische [3+2]-Cycloaddition der von α-Aminoestern abgeleiteten Schiff-Basen mit aktivierten Olefinen erfolgt in Gegenwart von AgHMDS/1. Die α-Aminoester-Schiff-Basen, darunter auch solche aus aliphatischen Iminen, liefern die jeweiligen Pyrrolidinderivate in hohen Ausbeuten sowie hoch exo- und enantioselektiv. EWG=elektronenziehende Gruppe, HMDS=Hexamethyldisilazid.

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