Get access

How to Make Five Contiguous Stereocenters in One Reaction: Asymmetric Organocatalytic Synthesis of Pentasubstituted Cyclohexanes

Authors

  • Efraím Reyes Dr.,

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author
  • Hao Jiang,

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author
  • Andrea Milelli,

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author
  • Petteri Elsner Dr.,

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author
  • Rita G. Hazell Dr.,

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author
  • Karl Anker Jørgensen Prof. Dr.

    1. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8619-6199
    Search for more papers by this author

  • This work was made possible by a grant from The Danish National Research Foundation and OChem School. E.R. thanks the “Eusko Jaurlaritza-Gobierno Vasco” for financial support (postdoctoral fellowship).

Abstract

original image

Give me five! In einer organokatalytischen Zweikomponenten-Dominoreaktion werden zwei C-C-Bindungen geknüpft und fünf Stereozentren aufgebaut (siehe Schema; DABCO = 1,4-Diazabicyclo[2.2.2]octan, TMS=Trimethylsilyl). Die Transformation zeichnet sich durch die starke Bevorzugung eines Diastereomers (aus 32 möglichen Isomeren) und Enantioselektivitäten bis 94 % aus.

Get access to the full text of this article

Ancillary