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Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

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.

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

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

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

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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

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Related Experiment Video

Updated: Jul 28, 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

Catalyst-Controlled Divergent Cycloisomerizations of

Yu Nie¹, Junrui Zhou¹, Youliang Wang¹

¹School of Chemistry, MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University (XJTU), Xi'an 710049, P. R. China.

Organic Letters

|June 5, 2023

Summary

This summary is machine-generated.

This study introduces a novel method for synthesizing indole derivatives using N-propargyl indoles and specific catalysts. The process allows for divergent cycloisomerizations, creating diverse molecular structures efficiently.

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Indole-tethered alkynes are versatile building blocks in organic synthesis.
Developing selective and efficient methods for cycloisomerization remains a key challenge.
Catalyst control offers a promising strategy for achieving divergent reaction pathways.

Purpose of the Study:

To develop a novel catalyst-controlled divergent cycloisomerization of N-propargyl indoles.
To explore the influence of catalyst properties (steric and electronic) on reaction outcomes.
To synthesize diverse libraries of pyrrolo[1,2-a]indoles and pyrrolo[3,2,1-ij]quinolines.

Main Methods:

Utilized N-propargyl indoles as substrates.
Employed BrettPhosAuNTf2 and PtCl4 as distinct catalysts.
Investigated catalyst-controlled divergent cycloisomerization reactions.

Main Results:

Successfully developed a new series of catalyst-controlled divergent cycloisomerizations.
Demonstrated chemodivergency attributed to catalyst steric and electronic properties.
Synthesized a broad spectrum of N-propargyl indoles into valuable heterocyclic scaffolds.
Achieved synthesis at millimolar scales.

Conclusions:

The developed protocol offers a flexible and efficient route to diverse indole-based heterocycles.
Catalyst selection is crucial for controlling the divergent cycloisomerization pathway.
This methodology provides a valuable tool for constructing complex molecular architectures.