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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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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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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Related Experiment Video

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Regioselective self-acylating cyclodextrins in organic solvent.

Eunae Cho1, Deokgyu Yun2, Daham Jeong2

  • 1Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea.

Scientific Reports
|March 30, 2016
PubMed
Summary

Amphiphilic cyclodextrins were synthesized without catalysts, showing regioselective acylation at the C2 position. This novel method creates nano-vesicles for potential drug delivery and functional surfactants.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

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Area of Science:

  • Carbohydrate Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Cyclodextrins (CDs) are cyclic oligosaccharides with a hydrophobic cavity and hydrophilic exterior.
  • Amphiphilic CDs possess both water-loving and water-hating properties, making them versatile for various applications.
  • Traditional synthesis of modified CDs often requires catalysts or harsh conditions.

Purpose of the Study:

  • To develop a novel, catalyst-free method for synthesizing amphiphilic cyclodextrins.
  • To investigate the regioselectivity and substrate preference during the self-acylation reaction.
  • To characterize the self-assembled supramolecular structures formed by amphiphilic CDs in water.

Main Methods:

  • Synthesis of amphiphilic cyclodextrins via self-acylation with vinyl esters in dimethylformamide.
  • Structural analysis using thin-layer chromatography (TLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS).
  • Characterization of nano-vesicular morphology using fluorescence spectroscopy, dynamic light scattering (DLS), and transmission electron microscopy (TEM).

Main Results:

  • Successful synthesis of amphiphilic cyclodextrins without the need for bases, catalysts, or enzymes.
  • Regioselective substitution predominantly occurred at the C2 position of the glucose unit, indicating catalytic activity of cyclodextrin.
  • Preference for long-chain acyl groups was observed, attributed to the cyclodextrin cavity's inclusion ability.
  • Formation of self-organized supramolecular architectures with nano-vesicular morphology in water.

Conclusions:

  • Cyclodextrins can act as regioselective catalysts in organic solvents for self-acylation reactions.
  • The developed synthetic method offers a novel route to mono-acylated cyclodextrins.
  • The resulting amphiphilic cyclodextrins self-assemble into nano-vesicles, showing promise for drug/gene delivery, functional surfactants, and carbohydrate derivatization.