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

被引：93
|
作者：
Hashihayata, T [1 ]
Ito, Y [1 ]
Katsuki, T [1 ]
机构：
[1] KYUSHU UNIV 33,FAC SCI,DEPT CHEM,HIGASHI KU,FUKUOKA 81281,JAPAN
来源：
TETRAHEDRON | 1997年 / 53卷 / 28期
关键词：
D O I：
10.1016/S0040-4020(97)00633-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：9541 / 9552
页数：12
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