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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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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.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

1.7K
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.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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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).
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Catalytic asymmetric Tamura cycloadditions.

Francesco Manoni1, Stephen J Connon

  • 1Trinity Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland).

Angewandte Chemie (International Ed. in English)
|February 28, 2014
PubMed
Summary

A novel catalyst enables the synthesis of valuable spirooxindole products from anhydrides and alkylidene oxindoles. This method offers excellent stereocontrol and broad applicability for diverse chemical structures.

Keywords:
asymmetric catalysiscycloadditionorganocatalysisspirocompoundssynthetic methods

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Spirooxindoles are important heterocyclic compounds with diverse biological activities.
  • Developing efficient and stereoselective methods for spirooxindole synthesis is a key challenge in organic chemistry.

Purpose of the Study:

  • To develop a novel catalytic system for the enantioselective synthesis of spirooxindoles.
  • To explore the scope and limitations of the developed methodology using various anhydride derivatives.

Main Methods:

  • Utilized a novel tert-butyl-substituted squaramide-based catalyst.
  • Investigated the reaction between enolizable anhydrides (homophthalic and glutaconic) and alkylidene oxindoles.
  • Analyzed the influence of reaction temperature on stereochemical outcomes.

Main Results:

  • Achieved excellent enantio- and diastereocontrol in the formation of spirooxindole products.
  • Demonstrated broad substrate scope, accommodating both homophthalic and glutaconic anhydride derivatives.
  • Observed a clean post-cyclization decarboxylation for glutaconic anhydride derivatives.
  • Identified an unusual temperature-dependent influence on diastereocontrol, yielding epimeric products at specific stereocenters with high optical purity.

Conclusions:

  • The novel squaramide catalyst effectively promotes the asymmetric synthesis of spirooxindoles.
  • The methodology provides access to structurally diverse spirooxindoles with high stereoselectivity.
  • Temperature plays a critical role in controlling diastereoselectivity, offering a tunable approach to epimeric products.