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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Multiple Halogenation of Methyl Ketones: Haloform Reaction

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Asymmetric hydroformylation.

Bernabé F Perandones¹, Cyril Godard, Carmen Claver

¹Departament de Química Física i Inorgánica, Universitat Rovira i Virgili, C/ Marcel.li Domingo s/n, 43007, Tarragona, Spain.

Topics in Current Chemistry

|April 19, 2013

Summary

This summary is machine-generated.

Rhodium catalysts with phosphite ligands excel in asymmetric hydroformylation, achieving high enantioselectivity for diverse alkenes. While BINAPHOS ligands are highly successful, reaction conditions can unexpectedly alter selectivity trends for complex substrates.

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Area of Science:

Organometallic Chemistry
Asymmetric Catalysis
Organic Synthesis

Background:

Rhodium-catalyzed hydroformylation is a key synthetic method for producing enantiomerically enriched aldehydes.
Ligand design has been crucial in achieving high enantioselectivity for various alkene substrates.
Phosphite-containing ligands, particularly phosphine-phosphites like BINAPHOS, have historically shown superior performance.

Purpose of the Study:

To review the state-of-the-art in rhodium-catalyzed asymmetric hydroformylation.
To highlight the role of ligands and reaction conditions in controlling enantioselectivity.
To identify remaining challenges and future directions in the field.

Main Methods:

Review of literature on rhodium-catalyzed hydroformylation.
Analysis of catalytic cycles and resting states.
Evaluation of ligand performance (diphosphites, phosphine-phosphites) with different alkene substrates.

Main Results:

Rhodium complexes with phosphite-based ligands, especially BINAPHOS derivatives, provide high enantioselectivity for many alkenes.
General trends in selectivity exist for substituted substrates, but can be reversed by optimizing catalysts and conditions.
The elucidation of catalytic mechanisms aids in understanding selectivity.

Conclusions:

Rhodium-catalyzed asymmetric hydroformylation is a powerful synthetic tool, largely due to advanced ligand development.
While significant progress has been made, achieving predictable and high enantioselectivity for all substrates remains challenging.
Further research into catalyst systems and reaction parameters is needed to overcome current limitations.