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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

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Updated: Mar 12, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Regiodivergent Catalysis: A Powerful Tool for Selective Catalysis.

Nico Funken¹, Yong-Qiang Zhang¹, Andreas Gansäuer¹

¹Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121, Bonn, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|November 5, 2016

Summary

Regiodivergent catalysis enables highly selective reactions with chiral substrates using enantiomerically pure catalysts. This approach generates constitutional isomers, offering significant potential for diversity-oriented synthesis.

Keywords:

catalysis diversity enantiomeric excess regiodivergent selectivity

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Area of Science:

Organic Chemistry
Catalysis
Stereochemistry

Background:

Chiral substrates present challenges in selective synthesis.
Controlling regioselectivity in reactions with enantiomers is crucial.

Approach:

Utilizing enantiomerically pure catalysts to interact distinctly with substrate enantiomers.
Employing regiodivergent catalysis for reactions involving racemic or enantiomerically enriched substrates.

Key Points:

Regiodivergent catalysis achieves highly regioselective formation of constitutional isomers.
Catalyst enantiomers interact differently with substrate enantiomers, mediating selectivity.
Enables parallel resolutions for racemic substrates and regioselective reactions for enantiopure substrates.

Conclusions:

Regiodivergent catalysis is a powerful tool for controlling chemical reactions.
This method significantly enhances functional and structural diversity in synthesis.
It provides valuable branching points for diversity-oriented synthesis (DOS).