Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition

Authors

  • Florian de Nanteuil,

    1. Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
    Search for more papers by this author
  • Prof. Dr. Jérôme Waser

    Corresponding author
    1. Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
    • Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/===

    Search for more papers by this author

  • EPFL, F. Hoffmann-La Roche Ltd and SNF (grant number 200021_129874) are acknowledged for financial support.

Abstract

original image

Fab Four: An iron-catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β-peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines.

Ancillary