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

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

5.2K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
5.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.3K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
13.3K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.8K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.8K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

4.0K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
4.0K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.1K
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...
18.1K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

3.0K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
3.0K

You might also read

Related Articles

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

Sort by
Same author

Novel 1,3,4-thiadiazoles inhibit colorectal cancer via blockade of IL-6/COX-2 mediated JAK2/STAT3 signals as evidenced through data-based mathematical modeling.

Cytokine·2018
Same author

Mentha-Stabilized Silver Nanoparticles for High-Performance Colorimetric Detection of Al(III) in Aqueous Systems.

Scientific reports·2018
Same author

Poly(lactic-<i>co</i>-glycolic acid)-loaded nanoparticles of betulinic acid for improved treatment of hepatic cancer: characterization, in vitro and in vivo evaluations.

International journal of nanomedicine·2018
Same author

Complicated jejunal diverticulitis with unusual presentation.

Radiology case reports·2018
Same author

Novel fused oxazepino-indoles (FOIs) attenuate liver carcinogenesis via IL-6/JAK2/STAT3 signaling blockade as evidenced through data-based mathematical modeling.

Life sciences·2018
Same author

Transcriptomic signature of drought response in pearl millet (Pennisetum glaucum (L.) and development of web-genomic resources.

Scientific reports·2018

Related Experiment Video

Updated: Mar 14, 2026

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

Indium-Mediated Stereoselective Allylation.

Dinesh Kumar1, Sandeep R Vemula1, Narayanaganesh Balasubramanian1

  • 1Department of Chemistry and Biochemistry, North Dakota State University , Fargo, North Dakota 58108-6050, United States.

Accounts of Chemical Research
|October 5, 2016
PubMed
Summary

This study details advancements in stereoselective indium-mediated reactions for synthesizing chiral amines and related compounds. Researchers highlight practical methods, novel asymmetric chemistry, and mechanistic insights for efficient organic synthesis.

More Related Videos

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

8.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K

Related Experiment Videos

Last Updated: Mar 14, 2026

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
Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

8.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K

Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Organometallic Chemistry

Background:

  • Indium-mediated reactions offer practical conditions due to allylindium's moisture insensitivity.
  • Despite extensive research, opportunities exist for developing efficient and sustainable indium-based synthetic methods.
  • Chiral amines and related compounds are crucial building blocks in pharmaceuticals and materials science.

Purpose of the Study:

  • To present a comprehensive overview of indium-mediated synthetic methods for chiral amine preparation.
  • To highlight practical method development, novel asymmetric chemistry, and mechanistic understanding.
  • To stimulate further research in organoindium chemistry for organic synthesis.

Main Methods:

  • Indium-mediated allylation of chiral hydrazones and N-acylhydrazones using BINOL ligands for enantioselectivity.
  • Indium-mediated asymmetric intramolecular cyclization with amino acid additives.
  • Investigation of amino acid additives in indium-mediated allylation of isatins.
  • Palladium-catalyzed umpolung allylation of hydrazones with indium(I) iodide.

Main Results:

  • Achieved complete diastereoselectivity (>99:1) and quantitative yields in hydrazone allylation.
  • Developed enantioselective indium-mediated allylation of hydrazones and N-acylhydrazones with high enantioselectivity (up to 99% ee).
  • Synthesized biologically relevant chromanes with excellent diastereoselectivity (dr >99:1) via intramolecular cyclization.
  • Demonstrated efficient indium-mediated allylation of isatins yielding homoallylic alcohols with broad functional group tolerance.
  • Gained mechanistic insights into the role of amino acid additives and palladium-catalyzed umpolung allylation.

Conclusions:

  • Indium-mediated reactions provide a powerful and practical platform for stereoselective synthesis of valuable organic molecules.
  • The use of chiral ligands and additives significantly enhances enantioselectivity and reaction efficiency.
  • Mechanistic understanding is crucial for further optimization and application of organoindium chemistry.