Synthetic studies on strictamine: Unexpected oxidation of tertiary amine in Ru-catalyzed ring-closing olefin metathesis

Yoshiyuki Komatsu, Kei Yoshida, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

During synthetic studies toward strictamine, unexpected oxidation of tertiary amine to enamine was observed in ring-closing olefin metathesis (RCM) using Hoveyda-Grubbs 2nd catalyst. Control experiments under deoxygenated conditions indicated Ru-catalyst and electron deficient 1,4-benzoquinone additive promoted oxidation. The desired RCM reaction took place selectively under microwave irradiation by suppression of oxidation of amine.

Original languageEnglish
Pages (from-to)377-380
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number5
DOIs
Publication statusPublished - 2013 Jan 30

Keywords

  • Alkaloid
  • Amine
  • Enamine
  • Olefin metathesis
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthetic studies on strictamine: Unexpected oxidation of tertiary amine in Ru-catalyzed ring-closing olefin metathesis'. Together they form a unique fingerprint.

  • Cite this