The first asymmetric epoxidation using a combination of achiral (salen)manganese(III) complex and chiral amine

Takashi Hashihayata, Yoshio Ito, Tsutomu Katsuki

Research output: Contribution to journalArticle

95 Citations (Scopus)

Abstract

A new catalyst system for asymmetric epoxidation was developed by using an achiral (salen)manganese(III) complex with chiral amine. Commercially available (-)-sparteine showed the highest asymmetric induction over the other chiral amines examined and addition of water to the reaction medium improved the induction up to 73% ee in the epoxidation of chromene derivative. Application of the system to the asymmetric oxidation of methyl phenyl sulfide to its sulfoxide was a so examined (at most 25% ee). These results support our proposal that a non-planar and chiral structure of the salen ligand plays an important role in the enantioface selection of olefins by (salen)manganese(III) complex.

Original languageEnglish
Pages (from-to)9541-9552
Number of pages12
JournalTetrahedron
Volume53
Issue number28
DOIs
Publication statusPublished - Jul 14 1997

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sulfoxide
Epoxidation
Manganese
Amines
Sparteine
Benzopyrans
Alkenes
Ligands
Water
Derivatives
Oxidation
Catalysts
disalicylaldehyde ethylenediamine
N,N'-bis(salicylideneamino)ethane-manganese(II)
methylphenylsulfide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The first asymmetric epoxidation using a combination of achiral (salen)manganese(III) complex and chiral amine. / Hashihayata, Takashi; Ito, Yoshio; Katsuki, Tsutomu.

In: Tetrahedron, Vol. 53, No. 28, 14.07.1997, p. 9541-9552.

Research output: Contribution to journalArticle

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