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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.
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).
[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.
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.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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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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Gold-catalyzed transannular [4+3] cycloaddition reactions.

Benjamin W Gung1, Derek T Craft, Lauren N Bailey

  • 1Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, USA. gungbw@muohio.edu

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 26, 2009
PubMed
Summary

Researchers synthesized macrocyclic propargyl acetates using a chromium(II) chloride-promoted reaction. Gold catalysts facilitated a tandem rearrangement and cycloaddition, yielding regio- and diastereospecific products based on starting material structure and ring size.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Macrocyclic compounds are important in medicinal chemistry and materials science.
  • Developing efficient synthetic routes to complex macrocycles remains a challenge.
  • Propargyl acetates are versatile synthetic intermediates.

Purpose of the Study:

  • To develop a novel method for synthesizing macrocyclic propargyl acetates containing a furan ring.
  • To investigate the utility of gold catalysts in promoting tandem reactions.
  • To control the regio- and stereochemistry of the cycloaddition products.

Main Methods:

  • Preparation of macrocyclic propargyl acetates via CrCl(2)-promoted reaction.
  • Application of Au(I) or Au(III) catalysts to induce tandem 3,3-rearrangement/transannular [4+3] cycloaddition.
  • Analysis of reaction products to determine regiochemistry and stereochemistry.

Main Results:

  • Successful synthesis of macrocyclic propargyl acetates with furan moieties.
  • Gold catalysis enabled a tandem 3,3-rearrangement and transannular [4+3] cycloaddition.
  • Products exhibited high regio- and diastereospecificity.
  • Regiochemistry was dictated by the acetoxy group's position; stereochemistry depended on ring size.

Conclusions:

  • A novel and efficient synthetic strategy for macrocyclic propargyl acetates was established.
  • Gold-catalyzed tandem reactions offer a powerful tool for constructing complex cyclic structures.
  • The developed method provides precise control over product stereochemistry and regiochemistry.