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Related Concept Videos

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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[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.
10.8K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
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.
2.8K
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
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.8K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.8K

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Pd-catalyzed asymmetric (6+2) dipolar cyclization for medium-sized spirooxindoles.

Yu-Qing Xiao1, Zi-Qing Li1, Fang Hu2

  • 1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China. luliangqiu@ccnu.edu.cn.

Chemical Communications (Cambridge, England)
|July 11, 2025
PubMed
Summary

This study introduces a new Pd-catalyzed method for synthesizing chiral spirooxindoles, specifically eight-membered lactones, using vinyloxetanes and diazo compounds. The efficient process yields highly enantioenriched products under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Medicinal Chemistry

Background:

  • Chiral spirooxindoles are crucial structural motifs in many biologically active compounds.
  • Efficient synthetic strategies for functionalizing spirooxindoles, particularly medium-sized spirocycles, are limited.

Purpose of the Study:

  • To develop a novel palladium-catalyzed asymmetric (6+2) dipolar cyclization reaction.
  • To synthesize enantioenriched spirooxindoles containing eight-membered lactone rings.

Main Methods:

  • Employing a Pd-catalyzed asymmetric (6+2) dipolar cyclization between vinyloxetanes and 3-diazoquinoline-2,4-diones.
  • Utilizing a tailored chiral phosphine ligand for high enantioselectivity.
  • Generating ketene dipolarophiles *in situ* via photochemistry.

Main Results:

  • Successfully synthesized enantioenriched spirooxindoles with eight-membered lactones.
  • Achieved high yields (up to 90%) and excellent enantioselectivities (up to 98% ee) for 22 examples.
  • Demonstrated the reaction proceeds under mild conditions.

Conclusions:

  • The developed method offers an efficient and versatile route to valuable chiral spirooxindole scaffolds.
  • This strategy addresses the scarcity of methods for functionalizing medium-sized spirocycles.
  • The use of *in situ* generated ketenes and chiral ligands enables high stereocontrol.