The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

Abstract

Over the years, the oxidative ring enlargement of furfuryl alcohols, known as the Achmatowicz reaction, has been developed into a powerful and versatile synthetic tool for the preparation of 6-hydroxypyranones. This review provides a comprehensive collection of the various ways to perform Achmatowicz rearrangement reactions and explores the role of this ring-expansion process in contemporary organic synthesis.

1 Introduction

2 Classical Methods and Variants

3 Single-Electron-Transfer Oxidations

4 Metal-Catalyzed Ring Expansions

5 Photolytic Oxygenations

6 Enzymatic Transformations

7 Conclusions

Key words

Achmatowicz reaction - ring expansion - furan - pyranone - synthetic methodology - heterocyclic chemistry

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