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Related Concept Videos

SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

9.0K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.0K
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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Sharpless Epoxidation02:57

Sharpless Epoxidation

4.3K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
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Prochirality02:05

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...
4.0K
Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

18.0K
It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
18.0K

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Highly enantioselective synthesis controlled by spin-exchange interaction.

Yong Yan1, Melad Shaikh1, Matthew C Beard2

  • 1Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA 92182, USA.

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|June 18, 2025
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Summary

External magnetic fields can now control asymmetric synthesis. This method uses magnetic polarization to induce enantioselective crystallization of catalysts, achieving high enantiomeric excess (ee) in organic reactions without chiral reagents.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Magnetochemistry

Background:

  • Achieving absolute asymmetric catalysis controlled by external magnetic fields has been a long-standing goal in synthetic chemistry.
  • Chirality-induced spin selectivity (CISS) effect offers a potential mechanism for magnetic control over stereochemistry.

Purpose of the Study:

  • To develop a strategy for absolute asymmetric catalysis controlled by an external magnetic field.
  • To demonstrate the efficacy of this approach in highly enantioselective organic reactions.

Main Methods:

  • Utilizing a spin-exchange reaction mechanism driven by the CISS effect.
  • Employing an external magnetic field to polarize a ferromagnetic surface (FM).
  • Inducing enantioselective crystallization of racemic catalysts on the FM surface.

Main Results:

  • Achieved 90% enantiomeric excess (ee) in [3+2] cycloaddition reactions.
  • Obtained 89% ee in aldol reactions.
  • Demonstrated that the product's chirality is dictated by the magnetic field's polarization (~±150 mT).

Conclusions:

  • An external magnetic field can serve as a versatile tool for symmetry breaking in chemical synthesis.
  • This method enables highly enantioselective organic synthesis without the need for pre-enantioenriched reagents.
  • The strategy effectively controls absolute asymmetric catalysis through magnetically induced enantioselective crystallization.