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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.4K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.4K
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.
10.4K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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.
2.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.4K

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Updated: Aug 17, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

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Pericyclases for cycloaddition.

Bo Zhang1, Hui Ming Ge1

  • 1State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, School of Life Sciences, Chemistry and Biomedicine Innovation Center (ChemBIC), Nanjing University, China.

National Science Review
|December 15, 2022
PubMed
Summary
This summary is machine-generated.

This perspective reviews pericyclase enzymes, which catalyze cycloaddition reactions essential for total synthesis. It highlights recent research advancements and remaining challenges in this field.

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Area of Science:

  • Organic Chemistry
  • Biocatalysis
  • Enzymology

Background:

  • Cycloaddition reactions are fundamental transformations in organic chemistry.
  • These reactions are extensively employed in the total synthesis of complex molecules.
  • Pericyclases are enzymes that catalyze cycloaddition reactions.

Purpose of the Study:

  • To provide a comprehensive review of pericyclase research.
  • To highlight the role of pericyclases in catalyzing cycloaddition reactions.
  • To discuss current challenges and future directions in the field.

Main Methods:

  • Literature review of pericyclase-catalyzed cycloadditions.
  • Analysis of recent research publications.
  • Discussion of enzymatic mechanisms and applications.

Main Results:

  • Pericyclases offer efficient and stereoselective routes to cycloaddition products.
  • Significant progress has been made in discovering and engineering pericyclases.
  • Challenges remain in enzyme scope, activity, and scalability.

Conclusions:

  • Pericyclases represent a powerful tool for synthetic chemists.
  • Further research is needed to overcome existing limitations.
  • Enzyme engineering holds promise for expanding pericyclase utility.