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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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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.

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...

Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

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Updated: Jul 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Recent advances in oxasteroids chemistry.

Malika Ibrahim-Ouali¹

¹UMR 6180 CNRS. malika.ibrahim@univ-cezanne.fr

|May 15, 2007

Summary

Oxasteroids are compounds of interest due to their unique structures and biological effects. This review details recent advances in their synthesis, offering new avenues for research and development.

Area of Science:

Organic Chemistry
Medicinal Chemistry
Stereochemistry

Background:

Oxasteroids are a class of compounds characterized by unique stereochemical properties.
These compounds exhibit promising and often unpredictable biological activities, driving scientific interest.

Purpose of the Study:

To review recent advancements in the synthesis of oxasteroids.
To highlight the progress in both partial and total synthesis methodologies for oxasteroids.

Main Methods:

Literature review of recent synthetic strategies for oxasteroids.
Analysis of key developments in partial and total synthesis approaches.

Main Results:

Significant progress has been made in developing efficient synthetic routes for oxasteroids.

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Novel methodologies for constructing the complex oxasteroid scaffold have been reported.

Conclusions:

Recent synthetic developments have expanded the accessibility of oxasteroids.
Further exploration of oxasteroid synthesis will likely uncover new biological applications.