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

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

You might also read

Related Articles

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

Sort by

Same author

Elucidating Formation Mechanisms of Inorganic Sulfates upon OH Radical Oxidation of Organosulfates via Non-Sulfur Radical Pathways: Insights from Methyl Sulfate.

Journal of the American Chemical Society·2026

Same author

α-C(sp<sup>3</sup>)-H Acetalization of Cyclic and Aliphatic Ethers Mediated by <i>N</i>-Bromoamides.

Organic letters·2026

Same author

Atroposelective Bromination for the Synthesis of Chiral Biaryl Phosphines via Cross-Assembled Catalysis with Chiral Phosphoric Acid and Achiral Phenol.

Journal of the American Chemical Society·2026

Same author

Efficient and Precise Force Field Optimization for Biomolecules Using DPA-3.

Journal of chemical information and modeling·2026

Same author

Terminal-Flip Monte Carlo: Accelerating the Convergence of Molecular Dynamics and Alchemical Free Energy Calculations.

Journal of chemical theory and computation·2026

Same author

Twenty Years of the Asian Core Program on Cutting-Edge Organic Chemistry in Asia (ACP-CEOCA): A Retrospective of the Last Decade.

Chemistry, an Asian journal·2026

Same journal

Decoding Galectin-Glycan Recognition with <sup>19</sup>F-Tagged Lectins: from Simple Glycans to the Cellular Glycocalyx.

Journal of the American Chemical Society·2026

Same journal

Open- and Closed-Shell Roles of Sensitizer and Annihilator in Pseudo-Single Component Mixtures for Upconversion.

Journal of the American Chemical Society·2026

Same journal

Pressure-Induced Superconductivity at 15 K in van-der-Waals Ferroelectric CuInP<sub>2</sub>S<sub>6</sub>.

Journal of the American Chemical Society·2026

Same journal

Carbene Analogues of Group 15: Reduction of s-Hydrindacene-Based Chloropnictogenium Ions To Access an Antimony Hydride Monocation and a Trinuclear Bismuth Dication.

Journal of the American Chemical Society·2026

Same journal

Chiral-Ligand-Modulated Nickel-Catalyzed Stereoselective Radical Migratory C2-Arylation of Carbohydrates.

Journal of the American Chemical Society·2026

Same journal

Coordination-Constraint-Driven Enhanced Chirality Induction in Perovskite Quantum Dot Solids.

Journal of the American Chemical Society·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Oct 25, 2025

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

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

Published on: February 7, 2019

A Catalyst-Controlled Enantiodivergent Bromolactonization.

Yuk-Cheung Chan¹, Xinyan Wang¹, Ying-Pong Lam¹

¹Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong, China.

Journal of the American Chemical Society

|August 5, 2021

Summary

This summary is machine-generated.

This study introduces a novel catalyst-controlled method for asymmetric bromolactonization of olefinic acids. A simple switch in catalyst structure completely reverses the stereochemical outcome, yielding enantiomerically pure lactones.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 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: Oct 25, 2025

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

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

Published on: February 7, 2019

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 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
Asymmetric Catalysis
Synthetic Methodology

Background:

Enantioselective synthesis is crucial for pharmaceuticals and agrochemicals.
Developing catalysts that control stereochemistry is a key challenge.
Bromolactonization offers a route to valuable lactone products.

Purpose of the Study:

To develop a catalyst-controlled enantiodivergent bromolactonization of olefinic acids.
To investigate the effect of catalyst structure on stereochemical outcome.
To elucidate the reaction mechanism.

Main Methods:

Utilized quinine-derived amino-amide catalysts.
Performed enantiodivergent bromolactonization of olefinic acids.
Conducted mechanistic studies including chemical experiments and DFT calculations.

Main Results:

Achieved catalyst-controlled enantiodivergent synthesis of lactones.
Demonstrated a complete switch in asymmetric induction by altering catalyst substituents.
Obtained desired lactones in good enantioselectivity and yield.

Conclusions:

The steric and electronic effects of catalyst substituents significantly influence the reaction mechanism.
This work provides a versatile method for accessing enantiomerically enriched lactones.
Catalyst design is critical for controlling stereochemistry in organic synthesis.