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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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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.
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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...
8.4K
Thermal Sigmatropic Reactions: Overview01:16

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2.1K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
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Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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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.
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Stereoselective Processes Based on σ-Hole Interactions.

Paola Peluso1, Victor Mamane2

  • 1Istituto di Chimica Biomolecolare ICB, CNR, Sede Secondaria di Sassari, Traversa La Crucca 3, Regione Baldinca, Li Punti, 07100 Sassari, Italy.

Molecules (Basel, Switzerland)
|July 27, 2022
PubMed
Summary

Sigma-hole interactions, crucial in controlling chirality, are explored for their role in stereoselective processes. This review highlights advancements in chiral supramolecular assemblies, enantiomer separation, and asymmetric catalysis.

Keywords:
chalcogen bondenantioselectivityenantioseparationhalogen bondnoncovalent interactionorganocatalysisrecognitionσ-hole

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Sigma-hole interactions are noncovalent forces involving atoms with electron-deficient regions (sigma-holes).
  • These interactions, particularly with halogens and chalcogens, are increasingly recognized for their role in molecular recognition and self-assembly.
  • Recent years have seen a surge in research demonstrating their influence on stereoselectivity.

Purpose of the Study:

  • To provide a comprehensive review of sigma-hole interactions in stereoselective processes.
  • To highlight recent advancements and applications in controlling chirality.
  • To consolidate knowledge on the utility of sigma-hole interactions in asymmetric synthesis and separation.

Main Methods:

  • Literature review of studies employing sigma-hole interactions.
  • Analysis of applications in chiral supramolecular assembly, enantiomer separation, and asymmetric catalysis.
  • Focus on experimental and computational evidence demonstrating stereochemical control.

Main Results:

  • Sigma-hole interactions are pivotal in directing the formation of chiral supramolecular structures.
  • These interactions facilitate the efficient separation of enantiomers.
  • Applications in enantioselective complexation and asymmetric catalysis have shown significant promise.

Conclusions:

  • Sigma-hole interactions offer a powerful tool for controlling stereochemistry in various chemical processes.
  • Further exploration of these interactions is expected to drive innovation in chiral technologies.
  • The review underscores the growing importance of noncovalent interactions in modern synthetic chemistry.