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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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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).

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 peroxy acids to...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

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Updated: Dec 28, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives.

Chunlan Song¹, Kun Liu¹, Xu Jiang¹

¹College of Chemistry and Molecular Sciences and The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, 430072, Hubei, P. R. China.

Angewandte Chemie (International Ed. in English)

|February 20, 2020

Summary

A new electrochemical method enables dearomative annulation of indoles, creating six-membered fused indolines. This oxidant- and metal-free approach offers a regioselective route to pyrimido[5,4-b]indoles for pharmaceutical applications.

Keywords:

[4+2] annulation dearomative annulation electrosynthesis indole pyrimido[5,4-b]indoles

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Dearomative annulation of indoles is crucial for synthesizing polycyclic indoline alkaloids.
Accessing six-membered-ring-fused indolines is challenging, especially under thermal conditions.

Purpose of the Study:

To develop an efficient electrochemical method for dearomative [4+2] annulation of indoles.
To access highly functionalized six-membered-ring-fused indolines, specifically pyrimido[5,4-b]indoles.

Main Methods:

Electrochemical dearomative [4+2] annulation between various indoles.
Oxidant- and metal-free reaction conditions.
Preliminary mechanistic studies involving radical intermediates.

Main Results:

A novel, regioselective, and stereoselective synthesis of pyrimido[5,4-b]indoles.
Excellent functional-group tolerance demonstrated.
The method is suitable for pharmaceutical research and modification tactics.

Conclusions:

Electrochemical dearomative annulation provides a powerful and efficient route to six-membered-ring-fused indolines.
The developed method offers advantages in terms of selectivity and reaction conditions.
This approach has potential applications in drug discovery and development.