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

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.6K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.6K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.5K
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.
3.5K
Turnover Number and Catalytic Efficiency01:19

Turnover Number and Catalytic Efficiency

21.6K
The turnover number of an enzyme is the maximum number of substrate molecules it can transform per unit time. Turnover numbers for most enzymes range from 1 to 1000 molecules per second. Catalase has the known highest turnover number, capable of converting up to 2.8×106 molecules of hydrogen peroxide into water and oxygen per second. Lysozyme has the lowest known turnover number of half a molecule per second.
Chymotrypsin is a pancreatic enzyme that breaks down proteins during digestion....
21.6K
Catalytically Perfect Enzymes01:07

Catalytically Perfect Enzymes

5.1K
The theory of catalytically perfect enzymes was first proposed by W.J. Albery and J. R. Knowles in 1976. These enzymes catalyze biochemical reactions at high-speed. Their catalytic efficiency values range from 108-109 M-1s-1. These enzymes are also called 'diffusion-controlled' as the only rate-limiting step in the catalysis is that of the substrate diffusion into the active site. Examples include triose phosphate isomerase, fumarase, and superoxide dismutase.
 
Most enzymes...
5.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.7K
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.
2.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.6K
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.
4.6K

You might also read

Related Articles

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

Sort by
Same author

Electrochemical synthesis of 2-oxa-bicyclo[2.1.1]hexanes by anodic oxidation-cyclization relay strategy.

Chemical science·2026
Same author

One-Pot Nucleophilic Organocatalytic Enantioselective [8 + 2] Cycloadditions of Photogenerated Ketenes with Triflate Tropolones.

Organic letters·2026
Same author

Stereoselective Higher-Order [10+4]- and [10+6] Cycloadditions Between Two Highly Unsaturated and Ambiphilic π-Addends.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Nucleophilic Activation of Cyclopropanes for Enantioselective Catalytic Transformations.

Accounts of chemical research·2026
Same author

Stereodivergent Inverse Electron-Demand Diels-Alder Reactions Enabled by Modification of Prolinol-Derived Catalysts.

Journal of the American Chemical Society·2026
Same author

Enantioselective Pd-Catalyzed Electrochemical Dearomative Allylation of Tropones: Construction of All-C Quaternary Stereocenters.

Organic letters·2026

Related Experiment Video

Updated: Feb 6, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

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

Published on: January 17, 2020

7.8K

Catalytic Enantioselective [10+4] Cycloadditions.

Bjarke S Donslund1, Nicolaj Inunnguaq Jessen1, Giulio Bertuzzi1

  • 1Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.

Angewandte Chemie (International Ed. in English)
|August 15, 2018
PubMed
Summary
This summary is machine-generated.

This study introduces the first catalytic [10+4] cycloaddition using amino isobenzofulvenes and dienes. The reaction demonstrates broad scope, high yields, and excellent stereoselectivity, driven by additive effects on intermediate rotamers.

Keywords:
asymmetric synthesiscycloadditiondensity-functional calculationsorganocatalysis

More Related Videos

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.7K
Preparation and 3D Tracking of Catalytic Swimming Devices
06:50

Preparation and 3D Tracking of Catalytic Swimming Devices

Published on: July 1, 2016

8.0K

Related Experiment Videos

Last Updated: Feb 6, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

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

Published on: January 17, 2020

7.8K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.7K
Preparation and 3D Tracking of Catalytic Swimming Devices
06:50

Preparation and 3D Tracking of Catalytic Swimming Devices

Published on: July 1, 2016

8.0K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Higher-order cycloadditions are crucial for constructing complex molecular architectures.
  • Developing catalytic and stereoselective variants of [10+4] cycloadditions remains a significant challenge in organic synthesis.

Purpose of the Study:

  • To describe the first peri- and stereoselective [10+4] cycloaddition reaction.
  • To utilize catalytically generated amino isobenzofulvenes as reaction partners with electron-deficient dienes.

Main Methods:

  • Employing a catalytic system for the generation of amino isobenzofulvenes.
  • Reacting these intermediates with various electron-deficient dienes in a [10+4] cycloaddition.
  • Conducting experimental and computational studies to elucidate the reaction mechanism and stereochemical control.

Main Results:

  • Achieved the first successful peri- and stereoselective [10+4] cycloaddition of this type.
  • Demonstrated a broad substrate scope with consistently high product yields.
  • Observed high levels of stereoselectivity, indicating a robust higher-order cycloaddition process.
  • Identified additive effects as critical for controlling enantioselectivity through kinetic distribution of intermediate rotamers.

Conclusions:

  • The developed catalytic [10+4] cycloaddition is a powerful method for synthesizing complex cyclic compounds.
  • The stereochemical outcome is governed by the kinetic control of intermediate rotamer populations, influenced by additives.
  • This work provides a robust platform for further exploration of higher-order cycloadditions in organic synthesis.