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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.
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.
[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.
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).
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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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

Published on: February 7, 2019

Recent advances in enantioselective [2 + 2 + 2] cycloaddition.

Takanori Shibata1, Kyoji Tsuchikama

  • 1Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 65-502B 3-4-1, Ohkubo, Shinjuku, Tokyo, 1698555, Japan.

Organic & Biomolecular Chemistry
|April 4, 2008
PubMed
Summary

Chiral transition metal catalysts enable enantioselective cycloadditions for creating complex molecules. This study highlights iridium and rhodium catalysts in novel alkyne and alkene cyclization reactions.

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Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Enantioselective cycloaddition reactions are vital for synthesizing chiral molecules.
  • Chiral transition metal catalysts offer atom-economical routes to complex structures.
  • Developing efficient methods for constructing chiral carbo- and heterocyclic skeletons remains a key challenge.

Purpose of the Study:

  • To disclose recent advancements in inter- and intramolecular enantioselective [2 + 2 + 2] cycloadditions.
  • To explore the use of chiral iridium and rhodium complexes in novel cyclization reactions.
  • To demonstrate the generation of axial chirality and quaternary carbons, including spirocyclic systems.

Main Methods:

  • Utilizing chiral iridium complexes for alkyne trimerization.
  • Employing chiral rhodium complexes for alkyne-alkyne-alkene cyclization.
  • Investigating both intermolecular and intramolecular reaction pathways.

Main Results:

  • Successful generation of axial chirality through iridium-catalyzed alkyne trimerization.
  • Efficient construction of quaternary carbon centers via rhodium-catalyzed cyclization.
  • Synthesis of complex spirocyclic systems with high enantioselectivity.

Conclusions:

  • Chiral transition metal catalysis provides powerful tools for enantioselective cycloadditions.
  • The developed methods offer efficient access to valuable chiral scaffolds.
  • This work expands the scope of asymmetric catalysis in organic synthesis.