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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

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.

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.

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.

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Related Experiment Video

Updated: Jun 28, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Recent Advances in π-Stacking Interaction-Controlled Asymmetric Synthesis.

¹State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.

Molecules (Basel, Switzerland)

|April 13, 2024

Summary

Pi-stacking interactions are crucial noncovalent forces in organic chemistry. This review highlights recent advances in pi-stacking controlled asymmetric synthesis, including chiral molecule construction.

Keywords:

asymmetric induction asymmetric synthesis diastereoselectivity π-stacking interaction

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

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Published on: February 7, 2019

Area of Science:

Organic Chemistry
Supramolecular Chemistry
Asymmetric Synthesis

Background:

Pi-stacking interactions are fundamental noncovalent forces in organic chemistry.
These interactions stabilize structures and transition states, influencing reaction selectivity (chemo-, regio-, stereoselectivities).

Purpose of the Study:

To review recent advancements in asymmetric synthesis controlled by pi-stacking interactions.
To showcase diverse applications of pi-stacking in creating complex chiral molecules.

Main Methods:

Literature review of recent studies on pi-stacking controlled reactions.
Focus on examples including auxiliary-induced synthesis, kinetic resolution, and synthesis of complex chiral architectures.

Main Results:

Demonstrated the pivotal role of pi-stacking in achieving high selectivity in various asymmetric transformations.
Highlighted successful applications in synthesizing challenging chiral molecules like helicenes and 3D chiral systems.

Conclusions:

Pi-stacking interactions offer powerful control in asymmetric synthesis.
Recent examples showcase the expanding utility of pi-stacking for constructing intricate chiral molecules and materials.