Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst

Yukie Nakamura, Hiromichi Egami, Kazuhiro Matsumoto, Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Chiral Ru(salen)(nitrosyl) complex 1 is a useful catalyst for asymmetric aerobic oxidation of alcohols under photo-irradiation. In this study, it was found that addition of β-hydroxy ketone or 1,3-diketone had a significant influence on its asymmetric catalysis. For example, the addition of 1,3-bis(p-bromophenyl)propane-1,3-dione 9 improved the relative reaction ratio in kinetic resolution of simple racemic secondary alcohols up to 30, while the addition gave an adverse effect on desymmetrization of an acyclic meso-1,3-diol. This additive effect was considered to be attributable to the chelate formation of the β-hydroxy ketone or 1,3-diketone with a Ru(salen) complex.

Original languageEnglish
Pages (from-to)6383-6387
Number of pages5
JournalTetrahedron
Volume63
Issue number28
DOIs
Publication statusPublished - Jul 9 2007
Externally publishedYes

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Ketones
Alcohols
Ligands
Propane
Catalysts
Kinetics
Catalysis
Irradiation
Oxidation
disalicylaldehyde ethylenediamine
ruthenium-N,N'-bis-(salicylidene)ethyl-enediaminato-nitrosyl complex

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst. / Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu.

In: Tetrahedron, Vol. 63, No. 28, 09.07.2007, p. 6383-6387.

Research output: Contribution to journalArticle

Nakamura, Yukie ; Egami, Hiromichi ; Matsumoto, Kazuhiro ; Uchida, Tatsuya ; Katsuki, Tsutomu. / Aerobic oxidative kinetic resolution of racemic alcohols with bidentate ligand-binding Ru(salen) complex as catalyst. In: Tetrahedron. 2007 ; Vol. 63, No. 28. pp. 6383-6387.
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