Iron-catalysed enantioselective carbometalation of azabicycloalkenes.

Chem Commun (Camb)

International Research Center for Elements Science, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto 611-0011, Japan and Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.

Published: July 2021

AI Article Synopsis

  • A new method has been developed for creating chiral organozinc intermediates using iron catalysis and azabicycloalkenes in an enantioselective carbometalation reaction.
  • The study shows how chiral phosphine ligands directly coordinate with iron during the reaction process, influencing the formation of bonds.
  • This innovative iron-catalyzed reaction is expected to aid in the synthesis of biologically active compounds.

Article Abstract

The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis to in situ form optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

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http://dx.doi.org/10.1039/d1cc02387jDOI Listing

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