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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Isocyanurates with planar chirality: design, optical resolution, and isomerization.

Hidetoshi Goto1, Masanao Sudoh, Keiko Kawamoto

  • 1Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Japan.

Chirality
|August 14, 2012
PubMed
Summary

Novel isocyanurates were synthesized using a unique concept to create atropisomeric molecules. These compounds were successfully resolved and their isomerization barriers were measured, showing bulky groups and bridging inhibit rotation.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Supramolecular Chemistry

Background:

  • C(s)-symmetric, prochiral planar molecules possess enantiotopic faces.
  • Differentiating these faces is key to creating chiral structures.
  • Atropisomerism offers a route to stable molecular chirality.

Purpose of the Study:

  • To design and synthesize novel atropisomeric isocyanurates.
  • To investigate the structural and stereochemical properties of these compounds.
  • To determine the rotational barriers and factors influencing isomerization.

Main Methods:

  • Synthesis of isocyanurates (1-3) based on differentiating enantiotopic faces.
  • Single-crystal X-ray diffraction for structural confirmation.
  • Chiral high-performance liquid chromatography (HPLC) for optical resolution.
  • Spectroscopic techniques (CD, UV-Vis, NMR, MS) for characterization.
  • Determination of rotational barriers (ΔG‡) via isomerization studies.

Main Results:

  • Isocyanurates 1 and 2(anti) exhibited planar chirality, confirmed by X-ray crystallography.
  • Optical resolution of all synthesized isocyanurates (1-3) was achieved.
  • Rotational barriers (ΔG‡) were measured: 27.2 kcal/mol (1), 27.6 kcal/mol (2), and 40.6 kcal/mol (3).
  • Compound 3 displayed the highest rotational barrier, indicating significant isomerization inhibition.

Conclusions:

  • A novel strategy for creating atropisomeric isocyanurates was successfully implemented.
  • Bulky substituents and intramolecular bridging effectively inhibit isomerization.
  • These findings contribute to the understanding and design of chiral molecules with restricted rotation.