Enantioselective electrocatalytic oxidation of racemic amines using a chiral 1-azaspiro[5.5]undecane N-oxyl radical

Yoshitomo Kashiwagi, Futoshi Kurashima, Chikara Kikuchi, Jun Ichi Anzai, Tetsuo Osa, James M. Bobbitt

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

A preparative electrocatalytic oxidation of racemic amines, which contain a chiral centre α to the amino group, on (6S, 7R, 10R)-4-acetylamino-2,2,7-trimethyl-10-isopropyl-1-aza-spiro[5.5]undecane N-oxyl yielded mixtures of carbonyl compounds (54.3-66.1%) and amines (33.9-45.7%) after 5 h of electrolysis, in which the current efficiency, turnover number, enantiopurity of the remaining (R)-isomers and S values were 90.7-94.8%, 21.7-26.5, 62-78% and 4.7-5.8, respectively.

Original languageEnglish
Pages (from-to)1983-1984
Number of pages2
JournalChemical Communications
Issue number19
DOIs
Publication statusPublished - 1999 Oct 7

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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