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

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...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 28; pp. 9541 - 9552
Main Authors Hashihayata, Takashi, Ito, Yoshio, Katsuki, Tsutomu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.07.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UNFUNCTIONALIZED OLEFINS
CATALYSIS
ENANTIOSELECTIVE EPOXIDATION
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Summary: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 also 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. Achiral (salen)manganese(III) complex was found to be a catalyst for asymmetric epoxidation under the influence of (−)-sparteine.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00633-9