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Axial-to-central chirality transfer in cyclization processes.

Damien Campolo¹, Stéphane Gastaldi, Christian Roussel

¹Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire UMR 7273, Equipe CMO, 13397 Cedex 20, Marseille, France. malek.nechab@univ-amu.fr michele.bertrand@univ-amu.fr.

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Summary

This summary is machine-generated.

Axially chiral molecules can be transformed into stereocenters through cyclization, transferring chirality. This method efficiently creates enantiopure carbocycles and heterocycles with high selectivity.

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Area of Science:

Organic Chemistry
Stereochemistry
Asymmetric Synthesis

Background:

Axial chirality is a type of chirality where chirality arises from the non-planar arrangement of atoms around an axis.
Transferring axial chirality to create new stereocenters is a key challenge in asymmetric synthesis.

Purpose of the Study:

To investigate the transfer of axial-to-central chirality during cyclization reactions.
To develop a strategy for synthesizing highly functionalized enantiopure carbocycles and heterocycles.

Main Methods:

Utilizing substrates with pre-existing axial chirality.
Performing intra- and inter-molecular cyclization reactions.
Analyzing regio- and stereo-selectivity of the transformations.

Main Results:

Successful synthesis of enantiopure carbocycles and heterocycles via axial-to-central chirality transfer.
Demonstrated high regio- and stereo-selectivity in the transformations of configurationally stable substrates.
Explored examples including allenes, biaryls, arylamides, and transient axially chiral species.

Conclusions:

The described strategy provides an effective route for asymmetric synthesis by transferring axial chirality.
The mechanistic rationale behind chirality transfer was elucidated, offering insights into the reaction pathways.