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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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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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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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Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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Updated: Jun 1, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Straightforward four-component access to spiroindolines.

Laurent El Kaïm1, Laurence Grimaud, Xavier-Frédéric Le Goff

  • 1UMR 7652 (Ecole Polytechnique/ENSTA/CNRS), Laboratoire Chimie et Procédés, Ecole Nationale Supérieure des Techniques Avancées, 32 Bd Victor, 75015 Paris, France. laurent.elkaim@ensta.fr

Chemical Communications (Cambridge, England)
|June 16, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel one-pot synthesis for spiroindolines using Ugi coupling and copper catalysis. This efficient method provides access to complex alkaloids with multiple points of molecular diversity.

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Published on: January 21, 2020

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Spiroindolines are important heterocyclic compounds with diverse biological activities.
  • Efficient synthesis of complex alkaloids remains a challenge in organic chemistry.

Purpose of the Study:

  • To develop a convenient and efficient method for synthesizing spiroindolines.
  • To access complex alkaloids with multiple points of molecular diversity.

Main Methods:

  • A one-pot procedure combining Ugi coupling and a copper-catalyzed oxidative process.
  • Synthesis performed at a peptidyl position.

Main Results:

  • Successful synthesis of spiroindolines via the described one-pot method.
  • The method provides straightforward access to complex alkaloids.
  • Four points of molecular diversity can be introduced.

Conclusions:

  • The developed method is a convenient and efficient route to spiroindolines.
  • This approach facilitates the synthesis of structurally diverse alkaloids.