Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives

Masayuki Iwasaki, Natsumi Miki, Yuichi Ikemoto, Yasuyuki Ura, Yasushi Nishihara

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.

Original languageEnglish
Pages (from-to)3848-3852
Number of pages5
JournalOrganic Letters
Volume20
Issue number13
DOIs
Publication statusPublished - Jul 6 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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