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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...

Chirality

Chirality

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.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

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.

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...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Related Experiment Video

Updated: Sep 4, 2025

Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition

Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition

Published on: October 3, 2018

Chirality enhances oxygen reduction.

Yutao Sang¹, Francesco Tassinari^1,2, Kakali Santra¹

¹Department of Chemical and Biological Physics, Weizmann Institute of Science, Rehovot 76100, Israel.

Proceedings of the National Academy of Sciences of the United States of America

|July 20, 2022

Summary

This summary is machine-generated.

Chiral electrodes boost oxygen reduction reaction (ORR) efficiency for clean energy. This spin selectivity effect lowers overpotentials and increases current densities, advancing fuel cell technology.

Keywords:

chirality fuel cells oxygen respiration spin

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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

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Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition

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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase

Published on: November 8, 2019

Area of Science:

Electrochemistry
Materials Science
Catalysis

Background:

Controlled oxygen reduction is crucial for clean energy technologies like fuel cells.
Oxygen reduction involves spin state transitions, necessitating consideration of spin constraints.
Aerobic organisms rely on controlled oxygen reduction for survival.

Purpose of the Study:

To investigate the impact of electrode chirality on the oxygen reduction reaction (ORR) efficiency.
To determine if chiral electrodes enhance electron transfer compared to achiral electrodes.
To explore the underlying mechanism of chirality-induced spin selectivity in ORR.

Main Methods:

Fabrication and characterization of chiral and achiral electrodes.
Electrochemical measurements, including overpotential and current density determination.
Analysis of electron transfer efficiency under varying electrode conditions.

Main Results:

Chiral electrodes exhibit significantly enhanced electron transfer efficiency for the oxygen reduction reaction compared to achiral electrodes.
Lower overpotentials and higher current densities were observed with chiral catalysts.
The observed enhancement persists even with heavy metal electrodes possessing large spin-orbit coupling.

Conclusions:

Chiral assemblies impart spin selectivity to the electron current, a phenomenon termed chiral-induced spin selectivity (CISS).
The CISS effect enhances the efficiency of the oxygen reduction reaction.
This finding offers a novel pathway for designing advanced catalysts for fuel cells and other clean energy applications.