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

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Published on: January 17, 2020

Catalytic enantiocontrol over a non-classical carbocation.

Roberta Properzi¹, Philip S J Kaib¹, Markus Leutzsch¹

¹Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.

Nature Chemistry

|September 29, 2020

Summary

Researchers achieved enantioselective control over non-classical carbocations using chiral acid catalysts. This breakthrough enables new catalytic methods for synthesizing valuable carbocation compounds with specific stereochemistry.

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Area of Science:

Organic Chemistry
Catalysis
Stereochemistry

Background:

Carbocations, including classical and non-classical types, are crucial intermediates in various chemical reactions.
Applications span the petroleum industry, drug discovery, and materials science.
Controlling stereochemistry in carbocation reactions is vital but challenging, especially for non-classical carbocations.

Purpose of the Study:

To develop the first enantioselective catalytic method for reactions involving non-classical carbocations.
To demonstrate the feasibility of controlling the stereochemical outcome of reactions proceeding through the non-classical 2-norbornyl cation.

Main Methods:

Utilized strong and confined chiral acids as catalysts.
Generated the non-classical 2-norbornyl cation intermediate from diverse precursors.
Leveraged non-covalent interactions between the catalyst and the carbocation intermediate.

Main Results:

Achieved unprecedented enantiocontrol over reactions involving the non-classical 2-norbornyl cation.
Demonstrated that structurally different precursors can yield the same enantioenriched product.
Showcased tailored catalysts as effective hosts for simple, non-functionalized carbocations.

Conclusions:

Strong and confined chiral acids can effectively catalyze enantioselective reactions via non-classical carbocations.
This work opens new avenues for catalytic synthesis of valuable enantioenriched carbocation systems.
The methodology provides a robust platform for future exploration of chiral carbocation chemistry.