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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.8K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.6K
Preparation of Epoxides03:00

Preparation of Epoxides

8.0K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
8.0K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.1K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

3.4K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
3.4K
Sharpless Epoxidation02:57

Sharpless Epoxidation

4.2K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Flavin-enabled reductive and oxidative epoxide ring opening reactions.

Bidhan Chandra De1,2, Wenjun Zhang1,2,3,4, Chunfang Yang1,2,3,4

  • 1Key Laboratory of Tropical Marine Bioresources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, China.

Nature Communications
|August 19, 2022
PubMed
Summary
This summary is machine-generated.

Fluostatins undergo non-enzymatic epoxide ring opening reactions catalyzed by flavin adenine dinucleotide (FAD) and nicotinamide adenine dinucleotide (NADH). This flavin chemistry offers new synthetic tools for organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Biochemistry

Background:

  • Epoxide ring opening is crucial in biology and synthesis, typically enzyme-catalyzed.
  • Flavin cofactors (FAD, NADH) are vital in redox reactions.

Purpose of the Study:

  • To investigate non-enzymatic epoxide ring opening of fluostatins.
  • To explore novel flavin-mediated reactions for organic synthesis.

Main Methods:

  • Studied fluostatin C's reaction with FAD and NADH.
  • Analyzed products formed via reductive and oxidative pathways.

Main Results:

  • Fluostatins undergo non-enzymatic epoxide ring opening with FAD/NADH.
  • Reductive and oxidative pathways yield diverse products (diols, ring-contracted/expanded products).
  • Reaction occurs in compounds with epoxides adjacent to conjugated carbonyl-aromatic systems.

Conclusions:

  • Discovered novel flavin-catalyzed epoxide ring opening reactions.
  • Findings expand flavin chemistry and offer new synthetic methodologies.