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Related Concept Videos

Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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...
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
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.
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.
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...

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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)

Published on: January 17, 2020

Enantioselective organocatalysis.

Matthew J Gaunt1, Carin C C Johansson, Andy McNally

  • 1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. mjg32@cam.ac.uk

Drug Discovery Today
|January 3, 2007
PubMed
Summary

Enantioselective organocatalysis offers a simple, safe, and effective alternative to metal catalysts for creating chiral molecules. This review highlights key catalytic strategies for synthesizing enantiomerically pure compounds.

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Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Enantioselective organocatalysis is a rapidly advancing field, providing sustainable alternatives to metal catalysis.
  • It offers operational simplicity, catalyst accessibility, and reduced toxicity for synthesizing chiral molecules.
  • This approach complements existing metal-catalyzed transformations in modern organic synthesis.

Purpose of the Study:

  • To review the impact of various organocatalyst classes in asymmetric synthesis.
  • To highlight strategic methodologies for constructing complex chiral molecules.
  • To emphasize the achievement of high enantiomeric purity using organocatalysis.

Main Methods:

  • Discussion of enamine catalysis mechanisms and applications.
  • Exploration of iminium ion catalysis for C-C and C-X bond formation.
  • Overview of nucleophilic and Brønsted acid catalysis in enantioselective transformations.

Main Results:

  • Demonstration of diverse chiral molecule synthesis using organocatalytic strategies.
  • Highlighting methods that achieve excellent enantioselectivity (high enantiomeric purity).
  • Showcasing the versatility of organocatalysis in accessing complex molecular architectures.

Conclusions:

  • Organocatalysis is a powerful and versatile tool for enantioselective synthesis.
  • It provides sustainable and practical routes to valuable chiral compounds.
  • Continued development promises further expansion of its synthetic utility.