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Related Concept Videos

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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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Aldol Condensation vs Claisen Condensation01:33

Aldol Condensation vs Claisen Condensation

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Aldol condensation is an acid or base-catalyzed condensation between aldehydes or ketones to give an α,ꞵ-unsaturated carbonyl compound. A base-promoted condensation between ester molecules to produce a ꞵ-ketoester is known as the Claisen condensation. In the presence of a base, both reactions involve deprotonation of the acidic α hydrogen to produce the corresponding enolates. The nucleophilic enolates attack their respective nonenolized carbonyl compound forming a tetrahedral...
5.8K
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

3.1K
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
3.1K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.7K
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

2.3K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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New methods of modification of α-cyclodextrin.

Bilge Deniz Özcan1, Morten Lang Zimmermann1, Mingzhe Ren1

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 København Ø, Denmark. bols@chem.ku.dk.

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|August 22, 2024
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Summary

Cyclodextrins are versatile carbohydrate-based molecules widely used in various applications. This review details current methods for synthetically modifying alpha-cyclodextrins, including direct and protection/deprotection strategies.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Cyclodextrins are ancient supramolecular hosts with enduring popularity in diverse fields.
  • Their widespread use stems from availability, biodegradability, water solubility, and carbohydrate origin.
  • Synthetic modifications are crucial for tailoring cyclodextrins for advanced applications.

Purpose of the Study:

  • To review state-of-the-art synthetic modification methods for alpha-cyclodextrin.
  • To cover techniques for both direct modification and those involving protection/deprotection strategies.

Main Methods:

  • Review of direct modification techniques on unprotected alpha-cyclodextrin.
  • Analysis of protection/deprotection strategies for regioselective modification.
  • Discussion of methods for attaching linkers, functional groups, lids, and bridges.

Main Results:

  • Comprehensive overview of current synthetic routes for alpha-cyclodextrin modification.
  • Highlights the versatility and adaptability of cyclodextrin chemistry.
  • Identifies key methodologies for creating complex cyclodextrin derivatives.

Conclusions:

  • Synthetic modification is essential for unlocking the full potential of cyclodextrins.
  • The reviewed methods provide a foundation for designing novel cyclodextrin-based materials and systems.
  • Advancements in modification techniques continue to expand cyclodextrin applications.