Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Prochirality

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...

Chirality at Nitrogen, Phosphorus, and Sulfur

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...

Chirality in Nature

Chirality in Nature

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.

Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Fluorinated carbohydrate-based vaccines.

Chemical science·2026

Same author

Photocatalytic, Regioselective Enone Deconjugation: An Enabling Platform for Terpene Modification.

Journal of the American Chemical Society·2026

Same author

Difluorinative Cyclopropene Rearrangement by I(I)/I(III) Catalysis: Regio- and Stereoselective Synthesis of Allyl Difluorides.

Angewandte Chemie (International ed. in English)·2025

Same author

Bio-inspired Deconjugative Isomerization of Borylated Dienoates.

Journal of the American Chemical Society·2025

Same author

Energy transfer-enabled enantioselective photocyclization using a privileged Al-salen catalyst.

Nature chemistry·2025

Same author

Enantioselective Photocatalysis Using a Privileged Al-Salen Complex.

Accounts of chemical research·2025

Same journal

A Domino-Synthesized Dicoordinate Copper(I) Bis-imidazopyridine Complex Triggering Cuproptosis/Ferroptosis for Enhanced Cancer Immunotherapy.

Angewandte Chemie (International ed. in English)·2026

Same journal

Mirror-Symmetric Organic Two-Dimensional Crystals for Alternative Photon Transport Pathways.

Angewandte Chemie (International ed. in English)·2026

Same journal

Cobalt-Catalyzed Migratory E-Selective Asymmetric Aza-Nozaki-Hiyama-Kishi Coupling.

Angewandte Chemie (International ed. in English)·2026

Same journal

Facile Synthesis of α,ω-Dihydroxy Telechelic Macromonomers From Ethylene and α-Olefins for Recyclable Alternating Block Copolymers.

Angewandte Chemie (International ed. in English)·2026

Same journal

Multi-Atom Sub-Nanometer Assemblies on Interpenetrating Multi-Chambered N/C Nanospheres.

Angewandte Chemie (International ed. in English)·2026

Same journal

A Synergistic C<sub>2+</sub> Alcohols/Olefins-Intermediated Pathway Boosts CO<sub>2</sub> Hydrogenation to Aromatics.

Angewandte Chemie (International ed. in English)·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Sep 13, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Privileged Chiral Photocatalysts.

Emanuel Studer¹, Smita Mandal¹, Timo Stünkel¹

¹Institute for Organic Chemistry, University of Münster, Corrensstrasse 36, 48149, Münster, Germany.

Angewandte Chemie (International Ed. in English)

|August 1, 2025

Summary

This summary is machine-generated.

Chiral catalysts enable asymmetric synthesis of small molecules. This review explores privileged chiral photocatalysts for excited-state reactions, bridging reactivity and selectivity.

Keywords:

Asymmetric photocatalysis Light‐enabled reactions Molecular design Non‐covalent interactions Privileged catalysts

More Related Videos

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Related Experiment Videos

Last Updated: Sep 13, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Area of Science:

Organic Chemistry
Catalysis
Photochemistry

Background:

Privileged chiral catalysts are crucial for asymmetric synthesis, enabling general and selective construction of small molecules.
These catalysts operate in the ground state, controlling reactivity and chirality with broad substrate scope.
Stereoselective photocatalysis has advanced significantly, creating a need for chiral catalysts active in excited states.

Purpose of the Study:

To survey the development of privileged chiral photocatalyst scaffolds.
To provide perspective on emerging chiral photocatalyst designs.
To address the challenge of reconciling reactivity and selectivity in excited-state catalysis.

Main Methods:

Literature review of privileged chiral photocatalyst scaffolds.
Analysis of catalyst evolution and design principles.
Discussion of challenges and future directions in chiral photocatalysis.

Main Results:

Identification of key chiral scaffolds enabling excited-state asymmetric catalysis.
Demonstration of the evolution from ground-state to excited-state privileged catalysts.
Highlighting the potential for new catalyst designs that bridge reactivity and selectivity.

Conclusions:

Developing privileged chiral catalysts for excited-state reactions is a critical frontier.
Chiral scaffolds must be validated for effective operation in non-ground state environments.
Future research will focus on reconciling reactivity and selectivity in photocatalytic asymmetric synthesis.