Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

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...
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
Regioselectivity and Stereochemistry of Hydroboration02:36

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.
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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 Acid-Catalyzed Hydration02:34

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.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Mastering the potential of well-defined ML<sup>1</sup>L<sup>2</sup> species in asymmetric catalysis through ligand immobilization (ML<sup>het</sup>L<sup>hom</sup>). Use in highly enantioselective Pd-catalyzed spiroannulation.

Chemical science·2026
Same author

Unlocking the Continuous Flow Asymmetric Hydrogenation of Olefins Through the Development of a Non-Deactivating Immobilized Iridium Catalyst.

Angewandte Chemie (International ed. in English)·2025
Same author

Photocatalyzed Ring Expansion of α-Ketosulfonylaziridines: Ready Access to δ-Sultams.

Angewandte Chemie (International ed. in English)·2025
Same author

Unlocking the Phosphoric Acid Catalyzed Asymmetric Transfer Hydrogenation of 2-Alkenyl Quinolines for Efficient Flow Synthesis of Hancock Alkaloids.

Organic letters·2025
Same author

Selective Aurora A-TPX2 Interaction Inhibitors Have <i>In Vivo</i> Efficacy as Targeted Antimitotic Agents.

Journal of medicinal chemistry·2024
Same author

Unlocking the Asymmetric Hydrogenation of Tetrasubstituted Acyclic Enones.

Angewandte Chemie (International ed. in English)·2023

Related Experiment Video

Updated: Jun 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

A solid-supported organocatalyst for highly stereoselective, batch, and continuous-flow Mannich reactions.

Esther Alza1, Carles Rodríguez-Escrich, Sonia Sayalero

  • 1Institute of Chemical Research of Catalonia (ICIQ), Avinguda dels Països Catalans 16, 43007 Tarragona, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 19, 2009
PubMed
Summary

A novel proline-functionalized resin catalyst enables highly stereoselective Mannich reactions. This efficient method simplifies product isolation and allows for continuous synthesis of pure Mannich adducts.

More Related Videos

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

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Related Experiment Videos

Last Updated: Jun 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Polymer Science

Background:

  • The Mannich reaction is a fundamental carbon-carbon bond-forming reaction in organic synthesis.
  • Developing efficient and stereoselective catalytic systems for the Mannich reaction remains a key challenge.
  • Immobilized catalysts offer advantages in terms of separation and recyclability.

Purpose of the Study:

  • To develop a highly stereoselective Mannich reaction using a novel proline-functionalized polymer-supported catalyst.
  • To investigate the influence of linker structure on catalyst performance.
  • To implement the reaction in a continuous-flow system for efficient synthesis.

Main Methods:

  • Synthesis of polystyrene resins functionalized with (2S,4R)-hydroxyproline using different linkers.
  • Evaluation of catalyst activity and stereoselectivity in Mannich reactions with aldehydes and ketones.
  • Optimization of reaction conditions, including microwave irradiation for ketone substrates.
  • Adaptation of the catalytic system for continuous-flow synthesis.

Main Results:

  • A 1,2,3-triazole linker proved optimal for catalytic activity and enantioselectivity.
  • Fast reactions (1-3 h) with high conversion were achieved for aldehyde donors.
  • Ketone reactions were accelerated by microwave irradiation.
  • Continuous-flow synthesis yielded enantiomerically and diastereomerically pure Mannich adducts (syn/anti>97:3; ee>99 %) with short residence times (6.0 min).

Conclusions:

  • The developed proline-functionalized resin catalyst provides an efficient and recyclable system for stereoselective Mannich reactions.
  • The methodology facilitates easy product isolation via filtration.
  • Continuous-flow synthesis offers a simplified and scalable approach for producing high-purity Mannich adducts.