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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

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Electrochemical Ferrier Rearrangement of Glycals.

Chun Qi¹, Giulio Goti¹, Andrea Sartorel¹

¹Department of Chemical Sciences, University of Padova, Via Francesco Marzolo 1, 35131 Padova, Italy.

Organic Letters

|October 21, 2024

Summary

We developed an electrochemical Ferrier rearrangement (FR) for synthesizing unsaturated glycosyl derivatives. This sustainable method offers broad substrate compatibility and high yields, advancing electrochemistry in sugar chemistry.

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Area of Science:

Carbohydrate Chemistry
Organic Electrochemistry
Synthetic Methodology

Background:

The Ferrier rearrangement (FR) traditionally uses harsh acids or oxidants.
Existing methods for synthesizing unsaturated glycosyl derivatives can be limited.
There is a need for more sustainable and versatile synthetic routes in carbohydrate chemistry.

Purpose of the Study:

To introduce a novel electrochemical approach to the Ferrier rearrangement.
To broaden the substrate scope and improve the efficiency of the FR.
To establish a sustainable alternative to traditional FR methods.

Main Methods:

Electrochemical oxidation of glycals.
In situ generation of reactive intermediates.
Reaction with various nucleophiles and glycal derivatives.

Main Results:

Successful electrochemical Ferrier rearrangement achieved.
Broad substrate compatibility demonstrated.
High yields and excellent diastereoselectivities obtained for 2,3-unsaturated glycosyl derivatives.

Conclusions:

The electrochemical FR is a viable and efficient alternative to traditional methods.
This sustainable approach expands the utility of electrochemistry in sugar synthesis.
The method provides a powerful tool for accessing diverse unsaturated glycosyl structures.