Synthesis 2020; 52(24): 3855-3865
DOI: 10.1055/s-0040-1707835
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Bin Wei
,
Ke-Wei Li
,
Yan-Chen Wu
,
Shi-Qi Tong
,
Ren-Jie Song
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China   eMail: srj0731@hnu.edu.cn
› Institutsangaben
We thank the National Natural Science Foundation of China (No. 21762030 and 51878326) for financial support. Ren-Jie Song was also supported by the China Scholarship Council (contract 201908360088).
Weitere Informationen

Publikationsverlauf

Received: 26. April 2020

Accepted after revision: 06. Mai 2020

Publikationsdatum:
08. Juni 2020 (online)


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