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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.

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

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.

Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

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Oxidation of Alcohols

Oxidation of Alcohols

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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...

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Related Experiment Video

Updated: Jun 16, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Published on: June 20, 2014

New modes for the osmium-catalyzed oxidative cyclization.

Timothy J Donohoe¹, Peter J Lindsay-Scott, Jeremy S Parker

¹Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom. timothy.donohoe@chem.ox.ac.uk

Organic Letters

|February 9, 2010

Summary

Osmium-catalyzed oxidative cyclization efficiently constructs pyrrolidines from amino alcohols using 4-nitropyridine N-oxide. This method yields enantiopure cis- and trans-pyrrolidines, offering a versatile route to substituted heterocyclic compounds.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Pyrrolidines are important heterocyclic scaffolds in pharmaceuticals and natural products.
Efficient and stereoselective synthesis of substituted pyrrolidines remains a key challenge in organic chemistry.

Purpose of the Study:

To develop a novel osmium-catalyzed oxidative cyclization for pyrrolidine synthesis.
To investigate the stereochemical outcomes of the cyclization using enantiopure starting materials.

Main Methods:

Osmium-catalyzed oxidative cyclization of amino alcohol precursors derived from 1,4-dienes.
Utilized 4-nitropyridine N-oxide (NPNO) as a novel reoxidant.
Employed enantiopure syn- and anti-amino alcohols to control stereochemistry.

Main Results:

Achieved effective construction of pyrrolidines via oxidative cyclization.
Demonstrated stereoselective formation of enantiopure cis- and trans-2,5-disubstituted pyrrolidines.
Showcased a complementary method for trans-pyrrolidine formation using bis-homoallylic amines with chelating groups.

Conclusions:

The developed osmium-catalyzed oxidative cyclization is a powerful tool for synthesizing substituted pyrrolidines.
The method provides access to enantiopure cis- and trans-pyrrolidines with high stereocontrol.
This approach expands the synthetic toolbox for constructing valuable nitrogen-containing heterocycles.