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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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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...
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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

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

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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.
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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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...
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Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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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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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Related Experiment Video

Updated: May 4, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
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Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues

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A shift in retrosynthetic paradigm.

Ilan Marek1

  • 1Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa, Israel. chilanm@tx.technion.ac.il

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 19, 2008
PubMed
Summary

This study introduces a novel synthetic strategy for creating complex molecules. It enables the formation of three new carbon-carbon bonds in a single step, efficiently generating enantiomerically pure compounds.

Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis
  • Synthetic Methodology

Background:

  • Current methods for synthesizing enantiomerically enriched all-carbon quaternary stereocenters in acyclic systems typically form one carbon-carbon bond per step using asymmetric catalysis.
  • These sophisticated methods are powerful but complex, often requiring multiple steps.

Purpose of the Study:

  • To propose a new retrosynthetic paradigm for the efficient synthesis of all-carbon quaternary stereocenters.
  • To develop a one-pot reaction capable of forming multiple carbon-carbon bonds simultaneously.

Main Methods:

  • Development of new synthetic pathways based on a novel retrosynthetic approach.
  • Utilizing classical reagents and standard experimental conditions.
  • Starting from common, readily available materials.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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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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Last Updated: May 4, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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

  • Demonstration of a one-pot reaction for the diastereoselective and enantioselective formation of three new carbon-carbon bonds.
  • Successful construction of all-carbon quaternary stereocenters in acyclic systems.
  • Achieved high stereochemical purity using conventional techniques.

Conclusions:

  • The proposed strategy offers a significantly different and potentially more efficient approach to synthesizing complex acyclic molecules.
  • This new paradigm simplifies the construction of challenging stereocenters, making them more accessible.
  • The method utilizes accessible starting materials and standard conditions, enhancing its practicality.