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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.
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Updated: Jun 28, 2025

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

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Published on: November 9, 2019

Stereoretentive enantioconvergent reactions.

Steven H Bennett¹, Jacob S Bestwick¹, Vera P Demertzidou¹

¹EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, UK.

Nature Chemistry

|April 17, 2024

Summary

This study introduces a novel enantioconvergent reaction strategy that retains substrate configuration, overcoming limitations of existing methods. This approach enables the synthesis of single enantioenriched products from racemic mixtures without stereochemical information loss.

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Last Updated: Jun 28, 2025

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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

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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Area of Science:

Organic Chemistry
Asymmetric Synthesis
Stereochemistry

Background:

Enantioconvergent reactions are crucial for asymmetric synthesis, converting both enantiomers of a racemic starting material into a single enantioenriched product.
Existing enantioconvergent methods typically require the loss of stereochemical information, limiting substrate scope to molecules with labile stereogenic units.

Purpose of the Study:

To develop a new enantioconvergent reaction approach that proceeds with full retention of the racemic substrate's configuration.
To challenge the established requirement of labile stereogenic units in substrates for enantioconvergent reactions.

Main Methods:

Developed a stereo-economic approach where two enantiomers of a racemic starting material are joined to form one enantiomer of a non-meso product.
Experimentally validated the concept through two distinct strategies: direct asymmetric coupling and a multicomponent approach.

Main Results:

Demonstrated a novel enantioconvergent reaction that preserves the stereochemical information of the racemic substrate.
The multicomponent approach exhibited statistical amplification of enantiopurity.
Successfully validated the concept, showing it is not limited to substrates with labile stereogenic units.

Conclusions:

The study presents a new paradigm in enantioconvergent synthesis, enabling reactions with full retention of substrate configuration.
This approach expands the scope of enantioconvergent reactions beyond molecules with labile stereogenic units.
The findings correct the dogma that labile stereogenic units are essential for enantioconvergent processes.