Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review

Published as part of the Special Topic Recent Advances in Metal-Catalyzed Ring Construction

Abstract

The γ-lactone skeleton is very important component of various natural products, biological molecules, food additives, and perfumes. As a result, much effort has been made towards such compounds. In this review, we summarize recent progress in transition-metal-catalyzed annulation reactions for the formation of γ-lactone derivatives through a radical pathway. Various reagents, such as anhydrides, Togni’s reagent, TMSN₃, arenesulfonyl chlorides, arenediazonium salts, dibenzoyl peroxides, O-benzoylhydroxylamine, NFSI, and α-halocarboxylic compounds, used in radical cyclization reactions are described, and the mechanisms of these radical annulation reactions are also discussed.

1 Introduction

2 Annulations of Alkenes with Anhydrides

3 Annulations of Unsaturated Carboxylic Acids with Nucleophiles

4 Annulations of Alkenes with α-Halocarboxylic Compounds

5 Conclusions and Outlook

Key words

transition metals - oxidation - radical reactions - annulations - γ-lactones - tetrahydrofuran-2-ones

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