Remote 1,6-Stereocontrol by Iminium-mediated Organocatalytic Events

Authors

  • Prof. Dr. Martin J. Lear,

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6566
    • Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6566

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  • Prof. Dr. Yujiro Hayashi

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6566
    • Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6566

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Abstract

original image

Control freaks: Chiral amine catalysts prove to be highly proficient mediators in the asymmetric, polyconjugate addition of C-, N-, and S-based nucleophiles to acyclic dienals and cyclic dienones. For high 1,6-selectivities, the stereo spatial matching of the molecular orbitals and ionic charges of the reacting species are key. But can we widen the scope and how far can we go with remote, iminium-stereocontrol?

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