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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
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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[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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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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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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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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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Dynamic Catalytic Highly Enantioselective 1,3-Dipolar Cycloadditions.

Okan Yildirim1,2, Michael Grigalunas1, Lukas Brieger3

  • 1Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.

Angewandte Chemie (International Ed. in English)
|July 8, 2021
PubMed
Summary

Researchers achieved enantioselective catalysis in dynamic covalent chemistry, enabling stereoselective synthesis of complex molecules. This breakthrough utilizes silver-catalyzed cycloadditions for creating multiple stereocenters with high selectivity.

Keywords:
asymmetric synthesisdiastereodivergent synthesisdynamic covalent chemistryenantiodivergent synthesispseudo-natural productsreversible cycloaddition

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Dynamic covalent chemistry relies on thermodynamic control and reversible bond formation.
  • Enantioselective catalysis in dynamic transformations is crucial for complex molecule synthesis but largely unexplored.
  • Previous methods lacked stereodivergent access to complex molecular architectures.

Purpose of the Study:

  • To discover and apply enantioselective catalysis in dynamic covalent 1,3-dipolar cycloaddition reactions.
  • To develop a stereodivergent tandem synthesis for complex molecules with multiple stereocenters.
  • To achieve high diastereoselectivity and enantioselectivity through asymmetric reversible bond formation.

Main Methods:

  • Utilized silver-catalyzed (Ag-catalyzed) 1,3-dipolar cycloadditions of azomethine ylides with electron-poor olefins.
  • Employed a tandem synthesis strategy involving two consecutive cycloaddition reactions.
  • Leveraged time-dependent reversible dynamic covalent-bond formation for stereochemical control.

Main Results:

  • Successfully developed a dynamic covalent enantioselective metal-complex-catalyzed 1,3-dipolar cycloaddition.
  • Achieved a stereodivergent tandem synthesis generating eight stereocenters with high diastereoselectivity and enantioselectivity.
  • Demonstrated enantiodivergent and diastereodivergent access to complex double cycloadducts from common reagents.

Conclusions:

  • This work pioneers enantioselective catalysis in dynamic covalent chemistry.
  • The developed method provides a powerful tool for synthesizing structurally and stereochemically complex molecules.
  • The strategy offers efficient access to diverse molecular architectures through asymmetric reversible bond formation.