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Electronic dissymmetry in chiral recognition.

Seth N Brown1, Everett T Chu, Michael W Hull

  • 1Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA. Seth.N.Brown.114@nd.edu

Journal of the American Chemical Society
|November 17, 2005
PubMed
Summary

Titanium complexes with beta-diketonate ligands exhibit electronic dissymmetry, enabling chiral recognition. This electronic effect, not steric hindrance, drives diastereoselectivity in titanium-BINOL complexes.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Stereochemistry

Background:

  • Beta-diketonate ligands in C2-symmetric titanium complexes create electronic dissymmetry.
  • The LUMO (Lowest Unoccupied Molecular Orbital) is a tilted dz2 orbital, influenced by titanium's configuration.

Purpose of the Study:

  • To investigate the role of electronic dissymmetry in chiral recognition.
  • To probe the diastereoselectivity of titanium-BINOL complexes.

Main Methods:

  • Synthesis of titanium-beta-diketonate complexes with 1,1'-bi-2-naphtholate (BINOL).
  • Nuclear Magnetic Resonance (NMR) spectroscopy to determine diastereomeric ratios.
  • Crystallography of related complexes to establish stereochemistry.

Main Results:

  • Titanium-BINOL complexes exclusively formed one diastereomer, as predicted by electronic factors.
  • Crystallography confirmed the predicted stereochemistry based on electronic grounds.
  • Tin analogues showed significantly lower diastereoselectivities, supporting electronic control.

Conclusions:

  • Electronic dissymmetry in titanium complexes is crucial for chiral recognition.
  • The observed diastereoselectivity is primarily governed by electronic effects, not steric factors.