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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Planar Chirality: A Mine for Catalysis and Structure Discovery.

Rosa López1, Claudio Palomo1

  • 1Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country (UPV/EHU), Manuel de Lardizabal 3, 20018, San Sebastián, Spain.

Angewandte Chemie (International Ed. in English)
|October 30, 2021
PubMed
Summary

Chemists are developing new catalytic methods to create planar chirality in strained molecules. This review highlights current techniques and inspires future advancements in asymmetric synthesis.

Keywords:
asymmetric catalysisatropisomerismcyclophanesmacrocyclizationplanar chirality

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Asymmetric Synthesis

Background:

  • Planar chirality is a key feature in nature and synthetic chemistry, enabling the creation of chiral reagents, catalysts, and materials.
  • Current synthetic methods often lack procedures to reliably induce and control asymmetry in planar chiral molecules.
  • This limitation has hindered the full exploitation of planar chirality's unique structural properties.

Purpose of the Study:

  • To review existing catalytic methods for generating planar chirality in strained organic molecules.
  • To inspire the development of novel, unconventional synthetic strategies for planar chiral compounds.
  • To address the challenges in controlling asymmetry during the synthesis of these molecules.

Main Methods:

  • Literature review of reported catalytic methods for inducing planar chirality.
  • Focus on methods applicable to strained molecular systems.
  • Analysis of the limitations and successes of current approaches.

Main Results:

  • Identified a limited but significant number of catalytic methods for producing planar chirality in strained molecules.
  • Demonstrated the potential of these methods despite inherent challenges in asymmetric induction.
  • Highlighted the structural diversity and functional applications of resulting planar chiral compounds.

Conclusions:

  • Catalytic methods for planar chirality in strained molecules are emerging but require further development.
  • There is a need for innovative procedures to enhance control over asymmetry in these syntheses.
  • Future research is expected to expand the scope and efficiency of planar chirality generation.