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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.

[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.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Diels–Alder Reaction: Characteristics of Dienes

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...

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Updated: Jul 12, 2025

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

Diastereodivergent Catalysis.

Daniel Moser¹, Tanno A Schmidt¹, Christof Sparr¹

¹Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.

|October 27, 2023

Summary

This summary is machine-generated.

This study explores catalyst-controlled diastereodivergence for creating complex molecules. It highlights dual catalysis strategies for efficiently accessing diverse stereoisomers, including alkenes and atropisomers.

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Last Updated: Jul 12, 2025

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

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

Organic Chemistry
Catalysis
Stereoselective Synthesis

Background:

Synthetic chemists face challenges in controlling relative stereochemistry for diastereomer synthesis.
Dual catalytic methods (sequential, relay, synergistic) offer efficient strategies for stereocontrol.

Purpose of the Study:

To discuss catalyst-controlled diastereodivergence in constructing carbon stereocenters.
To explore applications in atropisomeric systems and alkene geometry control.

Main Methods:

Review of illustrative examples demonstrating catalyst-controlled diastereodivergence.
Transfer of concepts to atropisomeric and alkene systems.

Main Results:

Catalyst control enables stereodivergent synthesis of diastereomers.
Dual catalysis is effective for controlling multiple stereogenic units.
Diastereodivergent catalysis extends to atropisomers and E/Z alkenes.

Conclusions:

Catalyst-controlled diastereodivergence is a powerful strategy in organic synthesis.
Dual catalytic approaches provide efficient access to diverse stereoisomers.
The principles are applicable to various stereogenic systems.