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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.
Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...
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.
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...

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A metal-catalyzed intermolecular [5+2] cycloaddition/Nazarov cyclization sequence and cascade.

Paul A Wender1, René T Stemmler, Lauren E Sirois

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu

Journal of the American Chemical Society
|February 10, 2010
PubMed
Summary

Researchers developed a novel metal-catalyzed [5+2] cycloaddition of vinylcyclopropanes (VCPs) and enynones. This efficient process provides facile access to the bicyclo[5.3.0]decane skeleton through combined cycloaddition and Nazarov cyclization reactions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The bicyclo[5.3.0]decane skeleton is a prevalent structural motif in natural products and biologically active molecules.
  • Efficient synthetic routes to this core scaffold are crucial for drug discovery and development.

Purpose of the Study:

  • To report the first metal-catalyzed [5+2] cycloaddition reactions between vinylcyclopropanes (VCPs) and enynones.
  • To develop efficient one-flask serial reactions and catalytic cascades for accessing the bicyclo[5.3.0]decane skeleton.

Main Methods:

  • Metal-catalyzed [5+2] cycloaddition of vinylcyclopropanes (VCPs) with enynones.
  • Subsequent Nazarov cyclization of the formed dienone cycloadducts.
  • Development of single-operation [5+2]/Nazarov serial reactions and catalytic cascades using a single catalyst.

Main Results:

  • Efficient formation of dienone cycloadducts from VCPs and enynones.
  • Successful application of these adducts in subsequent Nazarov cyclizations.
  • Demonstration of one-flask [5+2]/Nazarov serial reactions with improved efficiency (shorter reaction times, comparable or superior yields).
  • Identification of a single catalyst capable of mediating both transformations.

Conclusions:

  • The developed [5+2]/Nazarov reaction sequences offer a novel and facile synthetic strategy for the bicyclo[5.3.0]decane skeleton.
  • This methodology provides access to valuable scaffolds from simple and readily available starting materials.
  • The one-flask approach enhances synthetic efficiency and atom economy.