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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.

[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.

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

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...

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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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

An enantioselective four-component reaction via assembling two reaction intermediates.

Sifan Yu¹, Wenju Chang², Ruyu Hua¹

¹Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, PR China.

Nature Communications

|November 18, 2022

Summary

This study introduces a novel four-component reaction strategy for synthesizing complex molecules. The method efficiently couples in situ generated intermediates, offering a versatile approach to creating diverse chemical structures.

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Last Updated: Aug 20, 2025

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

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Published on: November 9, 2019

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Reaction intermediates are crucial but often unstable species in chemical transformations.
Identifying and characterizing these intermediates typically requires advanced analytical techniques.
Trapping experiments offer a powerful alternative for studying reactive intermediates and discovering new reactions.

Purpose of the Study:

To develop a novel multicomponent reaction strategy for generating complex molecular structures.
To explore the coupling of in situ generated iminium and enol intermediates.
To establish highly diastereoselective and enantioselective four-component reactions.

Main Methods:

Utilized a four-component reaction strategy involving alcohols, diazoesters, enamines/indoles, and aldehydes.
Employed trapping experiments to capture and study reactive intermediates.
Performed experimental and computational analyses to elucidate the reaction mechanism.

Main Results:

Successfully developed highly diastereoselective and enantioselective four-component reactions.
Generated over 100 examples of four-component reaction products.
Demonstrated mild reaction conditions with broad functional group tolerance.

Conclusions:

The presented method provides an efficient route to complex molecules via multicomponent reactions.
The strategy allows for the coupling of transiently generated iminium and enol intermediates.
A plausible reaction mechanism has been proposed based on comprehensive analyses.