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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
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

10.2K
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 Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
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.
3.9K
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

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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A Pd-Catalyzed Annulation Strategy to Linearly Fused Functionalized N-Heterocycles.

Larry Hoteite1, Benjamin D W Allen1, Ms Ergaiya A Elhajj1

  • 1The Department of Chemistry, The University of Sheffield, Sheffield, S3 7HF, U.K.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 6, 2024
PubMed
Summary
This summary is machine-generated.

We developed a palladium-catalyzed method to create fused polycyclic piperidines from simple precursors. This efficient strategy allows for selective functionalization and control over stereochemistry in synthesizing valuable nitrogen-containing molecules.

Keywords:
allylic alkylationcatalysisdiastereoselectiveenantioselectivepiperidine

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Linearly fused polycyclic piperidines are key structural motifs in many natural products and pharmaceuticals.
  • Developing efficient synthetic routes to these scaffolds is crucial for drug discovery and development.

Purpose of the Study:

  • To devise a novel palladium-catalyzed annulation strategy for synthesizing linearly fused polycyclic piperidines.
  • To enable control over enantioselectivity and diastereoselectivity in the synthesis.
  • To provide a method for chemoselective functionalization of the resulting scaffolds.

Main Methods:

  • Utilized a palladium-catalyzed annulation reaction.
  • Employed readily available 2-tetralones and indanones as starting materials.
  • Investigated conditions for controlling stereoselectivity (enantio- and diastereoselectivity).

Main Results:

  • Successfully synthesized linearly fused polycyclic piperidines.
  • Demonstrated the potential for controlling both enantio- and diastereoselectivity.
  • Showcased the chemoselective functionalization of the synthesized compounds.

Conclusions:

  • The developed Pd-catalyzed annulation strategy offers an efficient and robust method for accessing complex nitrogen-containing molecules.
  • This methodology facilitates the synthesis of valuable scaffolds with potential applications in medicinal chemistry.