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Correction: Thierry et al. Observation of Hyperpositive Non-Linear Effect in Asymmetric Organozinc Alkylation in Presence of <i>N</i>-Pyrrolidinyl Norephedrine. <i>Molecules</i> 2022, <i>27</i>, 3780.

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Hyperpositive non-linear effects: enantiodivergence and modelling.

Yannick Geiger1, Thierry Achard1, Aline Maisse-François1

  • 1Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg-CNRS, UMR 7504 Strasbourg France bellemin@unistra.fr.

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|June 7, 2021
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Summary
This summary is machine-generated.

Chiral ligand N-methylephedrine (NME) enables enantiodivergent catalysis for dimethylzinc addition to benzaldehyde. Varying catalyst loading or ligand enantiomeric excess (ee) controls product enantiomers, demonstrating a non-linear effect.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis
  • Organometallic Chemistry

Background:

  • Chiral ligands are crucial for enantioselective synthesis.
  • Controlling enantioselectivity in catalytic reactions remains a significant challenge.
  • The interplay between monomeric and dimeric catalyst species can influence reaction outcomes.

Purpose of the Study:

  • To investigate the enantiodivergent catalytic activity of N-methylephedrine (NME) in the addition of dimethylzinc to benzaldehyde.
  • To explore the influence of catalyst loading and ligand enantiomeric excess (ee) on product enantioselectivity.
  • To understand the mechanistic basis for enantiodivergence arising from monomeric and dimeric catalytic species.

Main Methods:

  • Enantioselective addition of dimethylzinc to benzaldehyde catalyzed by N-methylephedrine (NME).
  • Systematic variation of catalyst loading and ligand enantiomeric excess (ee).
  • Mathematical modeling and kinetic simulations to analyze reaction behavior.

Main Results:

  • NME demonstrated enantiodivergent catalysis, producing opposite product enantiomers by adjusting catalyst loading or ligand ee.
  • An enantiodivergent non-linear effect was observed, controllable by experimental parameters.
  • Simulations confirmed that simultaneous activity of monomeric and dimeric catalysts can lead to racemic products, even with enantioselective individual catalysts.
  • The observed kinetic constant (k_obs) showed unusual dependence on catalyst concentration and ligand ee, linked to monomer/dimer cooperative catalysis.

Conclusions:

  • The study highlights the potential for achieving enantiodivergence by manipulating monomer/dimer catalyst ratios.
  • Experimental conditions, specifically catalyst loading and ligand ee, are critical for controlling enantioselectivity in such systems.
  • The findings raise important questions about the generalizability of enantiodivergence in other systems involving simultaneous monomer and dimer catalysis.