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Catalyst control over pentavalent stereocentres.

Anton Budeev¹, Jianyang Dong¹, Daniel Häussinger¹

¹Department of Chemistry, University of Basel, Basel, Switzerland.

Nature Communications

|December 4, 2023

Summary

This summary is machine-generated.

Researchers developed a novel catalyst for controlling pentavalent stereocentres, expanding chemical synthesis possibilities. This breakthrough allows precise control over complex molecular configurations, previously a significant challenge in catalysis.

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Area of Science:

Stereochemistry
Catalysis
Organic Synthesis

Background:

Tetravalent stereocentres are well-controlled using various catalytic methods.
Controlling pentavalent stereocentres, which possess expanded stereochemical space, has been a persistent challenge in chemistry.

Purpose of the Study:

To demonstrate the catalytic control of pentavalent stereocentres.
To develop a method for enantioselective and diastereoselective synthesis of pentavalent compounds.

Main Methods:

A bifunctional iminophosphorane thiourea catalyst was designed and synthesized.
The catalyst was employed in reactions involving pentavalent phosphoranes to achieve stereocontrol.

Main Results:

The catalyst enabled enantioselective and diastereoselective synthesis of dioxophosphorane stereoisomers with high yields (up to 99%) and selectivity (up to 96:4 e.r. and 99:1 d.r.).
Stereodivergent catalysis was achieved, allowing selective access to different stereoisomeric states of pentavalent phosphoranes.

Conclusions:

Catalytic control over pentavalent stereocentres is feasible.
This work significantly expands the synthetically addressable stereochemical space, particularly for high-valent main group species.