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

Fingerprint

Esters
Chemical activation
Derivatives
Amides
Hydroxy Acids
Alkanes
Ethers
Photodegradation
Acetone
Benzene
Electric lamps
Light emitting diodes
Alcohols
Irradiation
Amino Acids

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

Cite this

Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C-H Bond Activation. / Ota, Eisuke; Mikame, Yu; Hirai, Go; Nishiyama, Shigeru; Sodeoka, Mikiko.

In: Synlett, Vol. 27, No. 7, 04.01.2016, p. 1128-1132.

Research output: Contribution to journalArticle

Ota, Eisuke ; Mikame, Yu ; Hirai, Go ; Nishiyama, Shigeru ; Sodeoka, Mikiko. / Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C-H Bond Activation. In: Synlett. 2016 ; Vol. 27, No. 7. pp. 1128-1132.
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