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

4.0K
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...
4.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.2K
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.
9.2K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
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...
5.0K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.3K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.3K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.3K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.3K
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

11.2K
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
11.2K

You might also read

Related Articles

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

Sort by
Same author

3D potassium energetic metal-organic framework enables safer lead-free primary energetic materials with positive oxygen balance.

Materials horizons·2026
Same author

Nitroimine-encoded conformational locking: a molecular switch for planarity and stability.

Materials horizons·2026
Same author

Synthesis, characterization, DFT calculations, and crystal structure of [Ru<sub>2</sub>(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub>(CO)<sub>4</sub> <i>L</i> <sub>2</sub>]: tri-fluoro-acetate-bridged dimeric ruthenium(I) sawhorse complexes bearing phosphine ligands.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Substrate and target selectivity of 4'-fluoroadenosine against viral and host polymerases.

The Journal of biological chemistry·2026
Same author

Topological Control of Dual Protonic-Electronic Conduction in Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same author

Structural insights into DENV-2 NS2B-NS3 protease and inhibition by glutathione-coated gold nanocluster.

Archives of virology·2026

Related Experiment Video

Updated: Mar 9, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.5K

Catalyst-Controlled Multicomponent Aziridination of Chiral Aldehydes.

Munmun Mukherjee1, Yubai Zhou1, Yijing Dai1

  • 1Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 23, 2016
PubMed
Summary

A new multicomponent aziridination method using chiral BOROX catalysts provides high control for synthesizing complex molecules. This reaction is effective for various chiral aldehydes, enabling the creation of valuable amino acid derivatives.

Keywords:
asymmetric catalysisaziridinesborox catalystcatalyst controlvapol

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.5K
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

10.0K

Related Experiment Videos

Last Updated: Mar 9, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.5K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.5K
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

10.0K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Chiral aldehydes are crucial building blocks in organic synthesis.
  • Developing stereoselective methods for functionalizing chiral aldehydes remains a significant challenge.
  • Multicomponent reactions offer efficient pathways to complex molecular architectures.

Purpose of the Study:

  • To develop a highly diastereoselective and enantioselective multicomponent aziridination method for chiral aldehydes.
  • To investigate the scope and limitations of the developed method with various substrates.
  • To demonstrate the utility of this reaction in the synthesis of non-natural amino acids.

Main Methods:

  • Utilized BOROX catalysts featuring VANOL (3,3'-diphenyl-2,2'-bi-1-naphthol) and VAPOL (2,2'-diphenyl-(4-biphenanthrol)) ligands.
  • Performed multicomponent aziridination reactions with a range of chiral aldehydes.
  • Analyzed reaction products for diastereoselectivity and enantioselectivity using analytical techniques.

Main Results:

  • Achieved highly diastereoselective and enantioselective aziridination of chiral aldehydes.
  • Demonstrated excellent catalyst control across diverse substrates, including those with α- and β-chiral centers.
  • Successfully synthesized epoxy aziridines, bis(aziridines), and ethylene diaziridines from chiral heterocyclic aldehydes.
  • Applied the method to synthesize β3-homo-d-alloisoleucine and β3-homo-l-isoleucine.

Conclusions:

  • The developed BOROX-catalyzed aziridination is a powerful and versatile method for stereoselective synthesis.
  • This approach provides efficient access to valuable chiral aziridines and complex amino acid derivatives.
  • The high catalyst control highlights the potential of VANOL and VAPOL ligands in asymmetric catalysis.