Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles

Ryoichi Kuwano, Nao Kameyama, Ryuhei Ikeda

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(η3-methallyl) 2(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

Original languageEnglish
Pages (from-to)7312-7315
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number19
DOIs
Publication statusPublished - May 18 2011

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Oxazoles
Imidazoles
Imidazolines
Gadiformes
Hydrogenation
Ruthenium
Chelation
Ligands
Catalysts

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles. / Kuwano, Ryoichi; Kameyama, Nao; Ikeda, Ryuhei.

In: Journal of the American Chemical Society, Vol. 133, No. 19, 18.05.2011, p. 7312-7315.

Research output: Contribution to journalArticle

Kuwano, Ryoichi ; Kameyama, Nao ; Ikeda, Ryuhei. / Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 19. pp. 7312-7315.
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