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[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.
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Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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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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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Multicomponent Hosomi-Sakurai Reaction on Isosorbide Derivatives.

Luca Banfi1, Lucia Garcia de la Parte2, Chiara Lambruschini1

  • 1Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy.

Molecules (Basel, Switzerland)
|June 26, 2026
PubMed
Summary
This summary is machine-generated.

This study optimized the Hosomi-Sakurai reaction for isosorbide derivatives, finding that tert-butyldiphenylsilyl ethers of the endo-OH group yield the best results for creating stable ether conjugates.

Keywords:
Hosomi-Sakuraibio-based compoundscarbohydratesdiastereoselectivityether synthesisisosorbidemulticomponent reactions

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

Published on: February 6, 2019

Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Materials Science

Background:

  • Isosorbide, a bio-based platform chemical, offers a sustainable scaffold for novel material synthesis.
  • Multicomponent reactions like the Hosomi-Sakurai reaction are powerful tools for constructing complex molecules efficiently.

Purpose of the Study:

  • To optimize the Hosomi-Sakurai reaction for monoprotected isosorbide derivatives.
  • To explore the synthesis of novel isosorbide-aldehyde conjugates with potential applications in materials science.

Main Methods:

  • Synthesis of trimethylsilyl ethers of monoprotected isosorbide derivatives.
  • Application of the Hosomi-Sakurai reaction using allyl trimethylsilane and various aldehydes.
  • Catalysis using trimethylsilyl triflate.

Main Results:

  • Optimal reaction conditions identified using TMS ethers of the endo-OH group.
  • Tert-butyldiphenylsilyl ether demonstrated superior performance as a protecting group.
  • Good yields and high diastereoselectivities achieved with aromatic and aliphatic aldehydes, with noted exceptions for sterically hindered or electron-poor aromatic aldehydes.

Conclusions:

  • The study establishes an efficient method for synthesizing isosorbide-aldehyde conjugates.
  • The developed method provides access to novel bio-based materials with stable ether linkages.
  • This work advances the utilization of isosorbide in sustainable chemical synthesis.