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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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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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Chiral Porous Sheet Assembly for Multiple Chirality Induction in Macrocycle Formation.

Yongsheng Li1, Tianyi Zheng1, Zhanting Li2

  • 1Department of Chemistry, State Key Lab of Molecular Engineering of Polymers, and Shanghai Key Lab of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438, China.

Journal of the American Chemical Society
|August 13, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for creating complex chiral macrocycles with multiple chiral centers. This technique utilizes confined macrocyclizations within chiral porous sheets, achieving high stereoselectivity for advanced molecular structures.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Stereochemistry

Background:

  • Chiral macrocycles with multiple chirality are vital for physical and biological applications.
  • Inducing multiple chirality during macrocyclization is a significant synthetic challenge.

Purpose of the Study:

  • To explore and establish a novel method for inducing multiple chirality in macrocyclization reactions.
  • To achieve excellent stereoselectivity in the synthesis of complex chiral macrocycles.

Main Methods:

  • Utilized self-assembled, single-layer chiral porous sheets formed by planar aromatic amphiphiles.
  • Employed confined macrocyclization within these chiral porous structures.
  • Leveraged the chiral environment to control substrate conformation and stereochemical outcomes.

Main Results:

  • Successfully generated macrocyclic products with multiple induced chiral centers.
  • Demonstrated excellent stereoselectivity in the macrocyclization process.
  • Achieved simultaneous induction of a stereocenter and strain-induced chirality.

Conclusions:

  • Confined macrocyclizations within chiral porous sheets offer a powerful strategy for synthesizing complex chiral macrocycles.
  • This approach overcomes previous limitations in multiple chirality induction.
  • The method provides a new pathway for creating molecules with tailored stereochemical properties.