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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit different...
Prochirality02:05

Prochirality

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...
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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Related Experiment Video

Updated: Jun 19, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Chiral (Stereoselective) Drugs, Asymmetric Synthesis, and Racemic Resolution Methods.

Burcu Karayavuz1, Cigdem Karaaslan Kirmizioglu1

  • 1Faculty of Gulhane Pharmacy, Department of Pharmaceutical Chemistry, University of Health Sciences, Ankara, Turkey.

Chirality
|June 17, 2026
PubMed
Summary
This summary is machine-generated.

Chiral drugs are crucial in medicine as different enantiomers can have varying effects. This review covers methods for creating single enantiomer drugs, ensuring both safety and efficacy in pharmaceutical development.

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Pharmaceutical Sciences

Background:

  • Chirality is fundamental in drug development, impacting biological targets and drug efficacy.
  • Enantiomers of a drug can exhibit different pharmacological activities, including therapeutic benefits, toxicity, or ineffectiveness.
  • The pharmaceutical industry increasingly focuses on single enantiomer drugs for improved safety and efficacy.

Purpose of the Study:

  • To review asymmetric synthesis and racemic resolution techniques for producing enantiomerically pure chiral drugs.
  • To provide examples from the pharmaceutical industry illustrating these methods.
  • To offer a comprehensive understanding of current approaches and challenges in chiral drug production.

Main Methods:

  • Asymmetric synthesis strategies for creating chiral molecules.
  • Racemic resolution techniques to separate enantiomers.
  • Analysis of methods used in the pharmaceutical industry for chiral drug development.

Main Results:

  • Summary of various synthetic and resolution methods for obtaining optically pure chiral compounds.
  • Highlighting the importance of enantiomeric purity for drug efficacy and safety.
  • Discussion of regulatory emphasis on evaluating individual enantiomer biological activity.

Conclusions:

  • Effective asymmetric synthesis and racemic resolution are critical for producing safe and effective chiral drugs.
  • The trend towards single enantiomer drugs necessitates advanced production techniques.
  • Understanding these processes is vital for pharmaceutical innovation and patient safety.