Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C-H Bond Activation

Eisuke Ota, Yu Mikame, Go Hirai, Shigeru Nishiyama, Mikiko Sodeoka

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

We developed a photo-chemical coupling reaction of α-keto esters with several simple alcohols, alkanes, ethers, and amides. Use of tertiary alkyl ester, α-cumyl ester, is the key for avoiding the known photo-degradation process. Intermolecular C-H bond activation and subsequent C-C bond formation were promoted by irradiation with an LED lamp (365 nm) without any additives. Among the coupling partners, reactions with sterically less demanding amides proceeded efficiently to provide unique N-acyl-β-amino-α-hydroxy acid derivatives. In benzene or acetone as a solvent, the reaction with a solid amino acid derivative provided a precursor of tetrahydro-1,4-diazepine-2,5-dione derivatives.

Original languageEnglish
Pages (from-to)1128-1132
Number of pages5
JournalSynlett
Volume27
Issue number7
DOIs
Publication statusPublished - 2016 Jan 4
Externally publishedYes

Keywords

  • C-H bond activation
  • coupling reactions
  • photo-chemical reaction
  • tetrahydro-1,4-diazepine-2.5-dione
  • α-cumyl esters
  • α-keto esters
  • β-amino acid derivatives

ASJC Scopus subject areas

  • Organic Chemistry

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