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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 Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Silver-Catalyzed Aldehyde Olefination Using Siloxy Alkynes.

Jianwei Sun¹, Valerie A Keller, S Todd Meyer

¹Department of Chemistry, University of Chicago, 5735 S. Ellis Ave, Chicago, IL 60637 Phone (+1)-773-7026886, Fax (+1)-773-7020805.

Advanced Synthesis & Catalysis

|November 26, 2013

Summary

This summary is machine-generated.

A new silver-catalyzed reaction efficiently synthesizes unsaturated esters using siloxy alkynes. This method offers an alternative to the Horner-Wadsworth-Emmons reaction, providing high selectivity and enabling sequential reactions.

Keywords:

Chemoselectevity Olefination Siloxy Alkyne Silver

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Organic Chemistry
Catalysis

Background:

The Horner-Wadsworth-Emmons reaction is a common method for synthesizing unsaturated esters.
Developing alternative, efficient, and selective olefination methods is crucial in organic synthesis.

Purpose of the Study:

To develop a novel silver-catalyzed carbonyl olefination reaction.
To synthesize trisubstituted unsaturated esters efficiently.
To provide an alternative to existing olefination methods.

Main Methods:

Utilized electron-rich siloxy alkynes in a silver-catalyzed reaction.
Employed various aldehydes with 1-siloxy-1-propyne or 1-siloxy-1-hexyne.
Investigated chemoselectivity in the presence of ester and ketone functionalities.

Main Results:

Achieved efficient synthesis of trisubstituted unsaturated esters.
Observed excellent diastereoselectivities for a range of aldehydes.
Demonstrated chemoselective olefination of aldehydes without by-product formation.
Showcased suitability for sequential reactions in a single flask.

Conclusions:

Developed a mild and efficient silver-catalyzed carbonyl olefination.
The new method is a viable alternative to the Horner-Wadsworth-Emmons reaction.
The process's mild conditions, high selectivity, and lack of by-products facilitate complex synthetic strategies.