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Atroposelective catalysis.

Tanno A Schmidt1, Valeriia Hutskalova1, Christof Sparr2

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Atropisomeric compounds, stereoisomers with restricted rotation, are crucial in medicinal chemistry and catalysis. This review covers catalyst-controlled synthesis of atropisomers, including complex systems with multiple stereogenic axes.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Catalysis

Background:

  • Atropisomeric compounds, defined by restricted bond rotation, are gaining prominence.
  • Their applications span medicinal chemistry, catalysis, and molecular nanoscience.
  • Recent interest fuels advancements in molecular motors and drug discovery programs.

Purpose of the Study:

  • To review catalyst-controlled stereoselective synthesis of atropisomers.
  • To highlight recent advancements and explore underdeveloped atropisomeric scaffolds.
  • To discuss complex systems with multiple stereogenic axes and higher-order stereogenicity.

Main Methods:

  • Generalizing synthetic methodologies for atropisomer synthesis.
  • Categorizing methods into desymmetrizations, kinetic resolutions, cross-coupling, and de novo ring formations.
  • Focusing on catalyst-controlled stereoselective approaches.

Main Results:

  • A diverse set of synthetic methodologies is available for atropisomer synthesis.
  • Recent advancements have expanded the scope of atroposelective reactions.
  • The review emphasizes scaffolds beyond C(sp2)-C(sp2) axes and complex stereogenic systems.

Conclusions:

  • Catalyst-controlled synthesis is key to accessing diverse atropisomers.
  • Further research into underdeveloped scaffolds and complex systems is warranted.
  • Atropisomers hold significant potential for future applications in various scientific fields.