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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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