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 - Jan 4 2016
Externally publishedYes

Fingerprint

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

All Science Journal Classification (ASJC) codes

  • 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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