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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...

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat...

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps. ...

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Esters to Alcohols: Hydride Reductions

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...

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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Updated: May 11, 2025

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

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Published on: January 17, 2020

Engineered Biocatalyst for Enantioselective Hydrazone Reduction.

Amy E Hutton^1,2, Fei Zhao¹, Elizabeth Ho³

¹Manchester Institute of Biotechnology and Department of Chemistry, University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK.

Angewandte Chemie (International Ed. in English)

|April 17, 2025

Summary

This summary is machine-generated.

Engineered imine reductases enable enantioselective reduction of hydrazones, offering a sustainable alternative to precious metal catalysts. This biocatalytic method yields valuable chiral hydrazine products with high efficiency and selectivity.

Keywords:

Biocatalysis Directed evolution Hydrazines Oxidoreductases Protein engineering

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Area of Science:

Biocatalysis
Organic Chemistry
Enzyme Engineering

Background:

Hydrazine-containing compounds are crucial in pharmaceuticals and agrochemicals.
Current synthesis methods often rely on expensive precious metals and harsh conditions.

Purpose of the Study:

To develop a biocatalytic method for enantioselective hydrazone reduction.
To engineer imine reductases for improved activity and selectivity.

Main Methods:

Screening of over 400 imine reductase (IRED) sequences.
Directed evolution to enhance enzyme performance.
Biocatalytic reduction of protected hydrazones.
Structural analysis of engineered enzymes.

Main Results:

Identification of a potent IRED variant (HRED1.1) through directed evolution.
HRED1.1 exhibits 20-fold higher activity than the parent enzyme.
High yields and enantioselectivities (>99% e.e.) achieved for various protected hydrazones.
Successful preparative scale biotransformations demonstrated.

Conclusions:

Engineered imine reductases provide a powerful and sustainable biocatalytic route for synthesizing chiral hydrazines.
This approach overcomes limitations of traditional chemical methods.
Expands the scope of biocatalysis for complex molecule synthesis.