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Related Concept Videos

Prochirality02:05

Prochirality

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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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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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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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Molecules with Multiple Chiral Centers

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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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Asymmetric Induction With Chiral Carbon-Bonding Donors.

Yuanling Pang1, Xinxin Li1, Hang Zhou1

  • 1School of Chemistry and Chemical Engineering, Shandong University, Jinan, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 23, 2026
PubMed
Summary

Chiral carbon bonding, a novel interaction in organic synthesis, has been demonstrated to induce asymmetry. This study validates carbon bonding as a feasible method for asymmetric induction, opening new avenues for chiral molecule synthesis.

Keywords:
asymmetric inductionbarbiturate skeletoncarbon bondingchiralnoncovalent interaction

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Area of Science:

  • Organic Synthesis
  • Supramolecular Chemistry
  • Asymmetric Catalysis

Background:

  • Carbon bonding is an emerging tool in organic synthesis.
  • Its capacity to induce chirality remains largely unexplored.
  • Understanding noncovalent interactions is crucial for developing novel synthetic methodologies.

Purpose of the Study:

  • To investigate the potential of carbon bonding to induce chirality.
  • To synthesize chiral carbon-bonding donors for proof-of-concept studies.
  • To demonstrate asymmetric induction using carbon bonding in a benchmark reaction.

Main Methods:

  • Synthesis of novel chiral carbon-bonding donor molecules.
  • Application of these donors in the oxa-Pictet-Spengler reaction.
  • Analysis of enantioselectivity in the reaction products.

Main Results:

  • Chiral carbon-bonding donors were successfully synthesized.
  • Asymmetric induction was observed over oxocarbenium ion intermediates.
  • Modest enantioselectivity was achieved in the initial proof-of-concept study.

Conclusions:

  • Carbon bonding can function as a noncovalent force for asymmetric induction.
  • This study validates carbon bonding as a viable strategy in asymmetric synthesis.
  • Further development holds promise for more efficient chiral synthesis methodologies.