Synthesis of γ‑Lactones Utilizing Ketoacids and Trimethylsulfoxonium Iodide

The Johnson–Corey–Chaykovsky epoxidation is one of the oldest methods for the synthesis of terminal epoxides from carbonyl compounds. Herein we present a simplified extension of the Johnson–Corey–Chaykovsky epoxidation, where ketoacids are employed as the substrates and commercially available trimet...

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (14), p.5533-5537
Main Authors: Triandafillidi, Ierasia, Savvidou, Anatoli, Kokotos, Christoforos G
Format: Article
Language:English
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Summary:The Johnson–Corey–Chaykovsky epoxidation is one of the oldest methods for the synthesis of terminal epoxides from carbonyl compounds. Herein we present a simplified extension of the Johnson–Corey–Chaykovsky epoxidation, where ketoacids are employed as the substrates and commercially available trimethylsulfoxonium iodide is employed as the carbon-atom homologating reagent. A variety of lactones are produced in a single step in synthetically useful yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01852