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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
2.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.3K
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.
10.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
3.6K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
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).
2.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.9K
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

2.6K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.6K

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Related Experiment Video

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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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Rh(I)-Catalyzed [5 + 2]/[2 + 2] Cycloaddition Cascade to Access a Cyclobutane-Fused [4-5-6-7] Tetracyclic Framework.

Bang-Hong Zhang1, Wen Bao1, Fu Cheng1

  • 1School of Pharmacy & State Key Laboratory of Applied Organic Chemistry & Collaborative Innovation Center for Northwestern Chinese Medicine, Lanzhou University, Lanzhou 730000, China.

Organic Letters
|April 4, 2023
PubMed
Summary

A new Rh(I)-catalyzed cascade reaction efficiently creates complex tetracyclic frameworks. This method rapidly builds three rings and four stereocenters, offering a novel synthetic strategy.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cycloaddition reactions are fundamental in organic synthesis for constructing cyclic molecules.
  • Developing efficient methods for creating complex polycyclic frameworks remains a significant challenge.
  • Rhodium(I)-catalyzed reactions offer unique reactivity for C-C bond formation.

Purpose of the Study:

  • To develop a novel Rh(I)-catalyzed cascade reaction for synthesizing highly strained tetracyclic frameworks.
  • To explore the formation of multiple rings, C-C bonds, and stereocenters in a single transformation.
  • To elucidate the mechanism of this complex cycloaddition cascade.

Main Methods:

  • Employing a Rh(I) catalyst to mediate a [5 + 2]/[2 + 2] cycloaddition cascade.
  • Utilizing specific substrates designed to undergo sequential cycloaddition and cyclization events.
  • Investigating reaction pathways through mechanistic studies, including intermediate analysis.

Main Results:

  • Successful synthesis of a complex [4-5-6-7] tetracyclic framework with good yields.
  • Achieved excellent diastereoselectivities in the formation of four contiguous stereocenters.
  • Demonstrated the efficient construction of three rings and three C-C bonds in one pot.
  • Identified Michael addition and Mannich reaction cascades as key mechanistic steps.

Conclusions:

  • The developed Rh(I)-catalyzed cascade reaction provides an efficient route to highly strained tetracyclic systems.
  • This methodology enables the rapid assembly of molecular complexity, including multiple stereocenters.
  • The mechanistic insights reveal the formation of sterically hindered cyclobutanes through a cascade of reactions.