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Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

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...

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

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...

Preparation of Epoxides

Preparation of Epoxides

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...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.

Sharpless Epoxidation

Sharpless Epoxidation

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...

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...

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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

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Published on: June 28, 2019

Iminologous epoxide ring-closure.

Chieh-Hung Tien¹, Alan J Lough², Andrei K Yudin¹

¹Davenport Research Laboratories, Department of Chemistry, University of Toronto Toronto ON M5S 3H6 Canada andrei.yudin@utoronto.ca.

Chemical Science

|November 9, 2022

Summary

This summary is machine-generated.

Chemists discovered a new reaction for synthesizing tetrasubstituted epoxides using nitrile-tethered precursors. This stereospecific reaction advances organic synthesis and understanding of chemical reactivity.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Reaction Discovery

Background:

Understanding fundamental chemical reactivity is crucial for advancing organic synthesis.
High-energy states, including reactive conformations, intermediates, and transition structures, are key areas of study.
Epoxide ring-closure is a well-established reaction in organic synthesis.

Purpose of the Study:

To explore a novel synthetic route for tetrasubstituted epoxides.
To investigate the incorporation of carbon-nitrogen (C≡N) functionality into epoxide precursors.
To elucidate the mechanism of this new epoxide ring-closure reaction.

Main Methods:

Synthesis of tetrasubstituted, nitrile-tethered epoxides.
Activation of iminologous diols followed by fragmentation.
Mechanistic studies to determine reaction stereospecificity.

Main Results:

Successful synthesis of tetrasubstituted epoxides featuring a nitrile tether.
The reaction proceeds via activation of iminologous diols and subsequent fragmentation.
The epoxide ring-closure transformation was found to be stereospecific.

Conclusions:

The discovered reaction provides a new method for synthesizing complex epoxides.
The stereospecificity supports a concerted mechanism for the epoxide ring-closure.
This work contributes to the understanding of fundamental chemical reactivity and organic synthesis.