Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.8K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.7K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.1K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
8.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.6K

You might also read

Related Articles

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

Sort by
Same author

Asymmetric 1,3-Dioxane Synthesis by Using Bifunctional Thiourea Catalysis.

Chemistry, an Asian journal·2026
Same author

Olefin-Catalyzed Aromatic Bromination toward Biocompatible Tyrosine Modification.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Mechanism-Guided Development of Bifunctional Cyclooctenes as Active, Practical, and Light-Gated Bromination Catalysts.

Chemistry (Weinheim an der Bergstrasse, Germany)·2024
Same author

BODNs as biocompatible brominating reagents: visible-light photocatalytic tyrosine modification under physiologically favorable conditions.

Chemical communications (Cambridge, England)·2024
Same author

Simultaneous Necking and Barreling Deformation Behaviors in Bending of Single-Crystal Gold Micro-Cantilever.

Materials (Basel, Switzerland)·2024
Same author

trans-Cyclooctenes as Scavengers of Bromine Involved in Catalytic Bromination.

Chemistry (Weinheim an der Bergstrasse, Germany)·2023

Related Experiment Video

Updated: Apr 15, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

7.5K

Facile net cycloaddition approach to optically active 1,5-benzothiazepines.

Yukihiro Fukata1, Keisuke Asano1, Seijiro Matsubara1

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan.

Journal of the American Chemical Society
|April 10, 2015
PubMed
Summary

Researchers developed a novel, highly enantioselective cycloaddition method for synthesizing 1,5-benzothiazepines. This breakthrough enables efficient production of optically active compounds for drug discovery and disease antagonism research.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.9K

Related Experiment Videos

Last Updated: Apr 15, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

7.5K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.9K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Asymmetric Synthesis

Background:

  • 1,5-benzothiazepine derivatives are recognized pharmacophores with potential therapeutic applications.
  • Developing enantioselective synthetic routes for these compounds is crucial for drug development.
  • Existing synthetic methods lack efficient enantioselective protocols for 1,5-benzothiazepines.

Purpose of the Study:

  • To establish the first enantioselective cycloaddition protocol for synthesizing 1,5-benzothiazepines.
  • To enable facile preparation of a diverse range of optically active 1,5-benzothiazepine derivatives.
  • To provide a scalable method for generating compound libraries for biological evaluation.

Main Methods:

  • Utilized chiral isothiourea catalysts to generate α,β-unsaturated acylammonium intermediates.
  • Employed a net [4 + 3] cycloaddition strategy.
  • Achieved two sequential chemoselective nucleophilic attacks by 2-aminothiophenols.

Main Results:

  • Successfully synthesized 1,5-benzothiazepines with high regioselectivity.
  • Demonstrated good-to-excellent stereoselectivity across various substrates.
  • Established a novel and efficient synthetic route for optically active 1,5-benzothiazepines.

Conclusions:

  • The developed protocol represents the first highly enantioselective net [4 + 3] cycloaddition for 1,5-benzothiazepines.
  • This method offers a versatile platform for constructing diverse libraries of optically active 1,5-benzothiazepines.
  • The findings provide a promising synthetic strategy for future drug discovery efforts targeting diseases.