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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Silver lining: Highly exo-selective asymmetric [3+2] cycloaddition of α-amino ester Schiff bases with activated olefins proceeds in the presence of AgHMDS/1. The α-amino ester Schiff bases including those derived from aliphatic imines successfully reacted to afford the corresponding pyrrolidine derivatives in high yield with high exo- and enantioselectivities. EWG=electron-withdrawing group, HMDS=hexamethyldisilazide.

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