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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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Lewis Acid-Driven Inverse Hydride Shuttle Catalysis.

Benjamin T Jones¹, Nuno Maulide¹

¹Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.

Angewandte Chemie (International Ed. in English)

|March 29, 2024

Summary

Inverse hydride shuttle catalysis enables efficient alkaloid synthesis but requires specific substrates. A new Lewis acid-driven method broadens substrate scope for complex azabicycle synthesis, including a total synthesis of (-)-tashiromine.

Keywords:

Asymmetric Cyclization Azabicycles Inverse Hydride Shuttle Lewis Acid Tashiromine

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Inverse hydride shuttle catalysis is a powerful tool for synthesizing alkaloid frameworks with high diastereoselectivity.
A key limitation of this method is the requirement for highly electron-deficient acceptors, restricting its applicability.

Purpose of the Study:

To develop a more general Lewis acid-driven approach to overcome the limitations of inverse hydride shuttle catalysis.
To enable the modular synthesis of complex azabicycles previously unattainable.

Main Methods:

A Lewis acid-driven strategy was developed to broaden the scope of inverse hydride shuttle catalysis.
Two modular synthetic strategies were employed to construct complex azabicyclic frameworks.

Main Results:

The new approach successfully addressed the limitation of electron-deficient acceptors.
Complex azabicycles, previously inaccessible, were synthesized modularly.
The enhanced synthetic flexibility enabled a streamlined asymmetric cyclization.

Conclusions:

A general Lewis acid-driven inverse hydride shuttle catalysis approach expands the synthetic utility of this method.
This work provides access to novel complex azabicycles and facilitates efficient total synthesis of alkaloids like (-)-tashiromine.