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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...

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

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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.

Stereochemical Effects of Enolization

Stereochemical Effects of Enolization

The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.

Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

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Updated: Jul 15, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Published on: November 9, 2019

Metal-Catalyzed Enantioconvergent Transformations.

Miguel Yus¹, Carmen Nájera¹, Francisco Foubelo^1,2

¹Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.

Chemical Reviews

|October 4, 2023

Summary

Enantioconvergent catalysis transforms racemic mixtures into single enantiomers using transition-metal catalysis. This review highlights recent advances in asymmetric synthesis, including cross-coupling and C-H functionalization methods.

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Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Enantioconvergent catalysis is crucial for synthesizing single enantiomers from racemic compounds.
Asymmetric synthesis aims to produce enantiomerically pure compounds, vital in pharmaceuticals and materials science.

Purpose of the Study:

To review recent advancements in enantioconvergent catalysis.
To cover transition-metal-catalyzed transformations for asymmetric synthesis.

Main Methods:

Radical-based cross-coupling of racemic alkyl electrophiles and nucleophiles.
Reductive cross-coupling of electrophiles using Ni/bis(oxazoline) catalysis.
Enantioconvergent C-H functionalization of racemic substrates.

Main Results:

Demonstrated enantioconvergent radical-based cross-coupling and reductive cross-coupling reactions.
Showcased enantioconvergent C-H functionalization strategies.
Highlighted hydroalkylation, hydrogen autotransfer, and other metal-catalyzed reactions like additions and hydroxylations.

Conclusions:

Enantioconvergent catalysis offers powerful tools for asymmetric synthesis.
Recent advances provide diverse methodologies for accessing single enantiomers from racemic starting materials.