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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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 surface of...
Alcohols from Carbonyl Compounds: Reduction02:23

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 (25–100°C) and...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium, dissociates into a...

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Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

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Multigram-Scale Asymmetric Alkene Reduction Catalyzed by a Thermostable Flavin Ene-Reductase.

Allison E Wolder1, Georg T Höfler1, Ombeline Mayol2

  • 1Biocatalysis Section, Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, Delft 2629 HZ, Netherlands.

Organic Process Research & Development
|June 25, 2026
PubMed
Summary

Old Yellow Enzymes (OYEs) enable sustainable chiral compound synthesis. This study achieved a record turnover number (TON) of 123,000 using a thermostable OYE for asymmetric reduction, overcoming previous scale-up limitations.

Keywords:
E-factorbiocatalysisene-reductasemonoterpenesold yellow enzymesscale-up

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

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

Published on: January 17, 2020

Area of Science:

  • Biocatalysis
  • Organic Chemistry
  • Enzyme Engineering

Background:

  • Old Yellow Enzymes (OYEs) are crucial biocatalysts for asymmetric alkene reduction, enabling sustainable synthesis of chiral compounds.
  • Limited turnover numbers (TONs) have hindered the industrial scale-up of OYE-catalyzed reactions.

Purpose of the Study:

  • To enhance the scalability of OYE-catalyzed asymmetric reductions.
  • To achieve high turnover numbers (TONs) and enantioselectivity in the reduction of monoterpenes using a thermostable OYE.

Main Methods:

  • Utilized a thermostable Old Yellow Enzyme (OYE) from *Thermus scotoductus* for asymmetric reduction reactions.
  • Performed multigram scale reactions (150 g/L) with a low enzyme loading (0.2 wt %).
  • Optimized reaction conditions for the reduction of (S)-carvone.

Main Results:

  • Achieved a record turnover number (TON) of 123,000 for an OYE-catalyzed reaction.
  • Obtained 90% isolated yield of (2R,5S)-dihydrocarvone from (S)-carvone.
  • Reached >99% enantiomeric excess for the product, demonstrating high stereoselectivity.
  • Reported an environmental E-factor of 11.6, indicating a relatively sustainable process.

Conclusions:

  • Demonstrated the successful scale-up of OYE-catalyzed asymmetric reduction with unprecedented TONs.
  • Highlighted the potential of thermostable OYEs for sustainable and efficient industrial production of chiral compounds.
  • Established a robust biocatalytic method for producing enantiomerically pure dihydrocarvone.