Dr. Vojtěch Dočekal and <a href="https://orgchem.natur.cuni.cz/vesely/">Prof. Jan Veselý</a> from the <a href="https://lcms.labrulez.com/companies/257">Department of Organic Chemistry</a>, <a href="https://lcms.labrulez.com/companies/16">Faculty of Science, Charles University</a> described a new highly efficient method for the preparation of planar chiral compounds.
The method based on organocatalytic desymmetrization was published in the prestigious journal <a href="https://www.nature.com/articles/s41467-024-47407-0">Nature Communications</a>. Congratulations!
Planar chiral [2.2]paracyclophanes contain two suitably substituted benzene nuclei linked at the para positions by ethylene bridges. Such compounds have a wide range of applications either as ligands or catalysts in synthetic chemistry, but also in materials science or medicine. Despite the wide range of applications, only a limited number of studies have been described for their preparation in enantiomerically pure form.
The methodology developed in the asymmetric synthesis group is based on the highly efficient desymmetrization of prochiral [2.2]paracyclophanes substituted with two formyl groups in suitable positions. In a key transformation, one of the prochiral aldehyde groups is selectively transformed to an ester, leading to the formation of a planar chiral product using asymmetric synthesis methods. Methodologies using catalysis by low molecular weight chiral catalysts derived from natural amino acids, more specifically using so-called N-heterocyclic carbenes, have proven to be highly effective for such asymmetric esterification.
In addition to the optimization of the methodology, a study of the scope of application of the developed transformation, or a study of the synthetic applicability of the chiral products, the publication includes a detailed experimental mechanistic study that reveals interesting differences in the reactivity of the starting diformyl[2.2]paracyclophanes.

An innovative approach to planar chiral substances

Article

Product

Events

Webinars

Application

Academy

Video

Poster

Scientists

Plastics

Environment

Food

Water

Health

Presentation

Scientific article

Interview

Toxicology

Popularization

Science and research

Software

Covid-19

Career

Laboratories

Various

Zaměření

Type of News

Focus

The Department of Organic Chemistry, Faculty of Science, Charles University is engaged in teaching and scientific research in the fields of synthetic organic chemistry, bioorganic and medicinal chemistry, materials chemistry, and electrochemistry.

Department of Organic Chemistry, Faculty of Science, Charles University

Pittcon 2026

36th MassSpec Forum Vienna 2026

US HUPO 2026

The science of next-gen ingredients: fermentation, formulation and function

The Data Driven Plant; How AI Transforms Chemical Manufacturing

Process Raman: A Reliable and Versatile Tool For Downstream Process Monitoring and Control For mAB Production