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Related Concept Videos

Cycloaddition Reactions: Overview01:16

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 Activation01:16

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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Pericyclic Reactions: Introduction01:17

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 rearrangements are...

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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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Gold-catalyzed Intermolecular [4C + 3C] Cycloaddition Reactions.

Benjamin W Gung1, Lauren N Bailey, Josh Wonser

  • 1Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056.

Tetrahedron Letters
|March 31, 2010
PubMed
Summary

N-heterocyclic carbene gold catalysts facilitate a direct [4C + 3C] cycloaddition between propargyl esters and dienes like cyclopentadiene and furan. This reaction efficiently forms seven-membered rings under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cycloaddition reactions are fundamental in organic synthesis for constructing cyclic molecules.
  • N-heterocyclic carbene (NHC) gold catalysts have emerged as powerful tools for various organic transformations.
  • Propargyl esters are versatile building blocks in organic synthesis.

Purpose of the Study:

  • To investigate the [4C + 3C] cycloaddition reaction of propargyl esters with cyclopentadiene and furan.
  • To explore the catalytic activity of N-heterocyclic carbene gold catalyst (NHC-AuIPr, 7) in this transformation.
  • To elucidate the reaction mechanism, distinguishing between direct cycloaddition and alternative pathways.

Main Methods:

  • Reaction of propargyl esters (1a-f, 13) with cyclopentadiene and furan.
  • Utilizing N-heterocyclic carbene gold catalyst (NHC-AuIPr, 7).
  • Analysis of reaction products and mechanistic studies.

Main Results:

  • Successful [4C + 3C] cycloaddition reaction observed under mild conditions.
  • Formation of seven-membered rings from propargyl esters and dienes.
  • Evidence supports a direct cycloaddition mechanism over cyclopropanation/Cope rearrangement.

Conclusions:

  • N-heterocyclic carbene gold catalysis enables an efficient [4C + 3C] cycloaddition of propargyl esters with cyclopentadiene and furan.
  • The reaction proceeds via a direct cycloaddition pathway.
  • This methodology offers a mild and effective route to seven-membered carbocyclic and heterocyclic compounds.