Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A novel type of photocyclization of α-ketoamides was developed, affording unique cyclopropanols bearing amide functionality. N-tert-Butyl, N-trityl, or N-non-substituted α-ketoamides with a bulky substituent at the β-position of the amide functionality were efficiently converted to corresponding cyclopropanols through the activation of the γ-C-H bond followed by C-C bond formation between the α- and γ-positions of the amide. Hydrogen abstraction from the γ-position of the amide was considered to be the rate-determining step of cyclopropanol formation, based on the kinetic isotope effect. Cyclopropanols could be converted to two different types of functionalized α-ketoamides depending on the method of ring-opening.

Original languageEnglish
Pages (from-to)5991-5994
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number44
DOIs
Publication statusPublished - 2015 Oct 28
Externally publishedYes

Fingerprint

Amides
Chemical activation
Bearings (structural)
Isotopes
Hydrogen
Kinetics
cyclopropanol

Keywords

  • Cyclopropanols
  • Kinetic isotope effect
  • Photo chemical reaction
  • Ring-opening reactions
  • α-Ketoamides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation. / Ota, Eisuke; Mikame, Yu; Hirai, Go; Koshino, Hiroyuki; Nishiyama, Shigeru; Sodeoka, Mikiko.

In: Tetrahedron Letters, Vol. 56, No. 44, 28.10.2015, p. 5991-5994.

Research output: Contribution to journalArticle

Ota, E, Mikame, Y, Hirai, G, Koshino, H, Nishiyama, S & Sodeoka, M 2015, 'Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation', Tetrahedron Letters, vol. 56, no. 44, pp. 5991-5994. https://doi.org/10.1016/j.tetlet.2015.09.038
Ota, Eisuke ; Mikame, Yu ; Hirai, Go ; Koshino, Hiroyuki ; Nishiyama, Shigeru ; Sodeoka, Mikiko. / Photo-induced formation of cyclopropanols from α-ketoamides via γ-C-H bond activation. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 44. pp. 5991-5994.
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