THREITOL-STRAPPED MANGANESE PORPHYRINS AS ENANTIOSELECTIVE EPOXIDATION CATALYSTS OF UNFUNCTIONALIZED OLEFINS

被引：150

作者：

COLLMAN, JP ^{[1
]}

LEE, VJ ^{[1
]}

KELLENYUEN, CJ ^{[1
]}

ZHANG, XM ^{[1
]}

IBERS, JA ^{[1
]}

BRAUMAN, JI ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 02期

关键词：

D O I：

10.1021/ja00107a013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nine members of a family of new chiral porphyrins have been prepared from reactions between ditosylthreitol derivatives and 5,10,15,20-tetrakis(2-hydroxyphenyl)porphyrin. The assignment of the resultant isomers has been made from their H-1 NMR spectra and on the basis of an absolute configuration determination from the crystal structure of 4. The chiral frameworks of these systems are easily varied by condensing different aldehydes and ketones with the 2,3-diol of the threitol unit. The manganese derivatives of six of these systems were studied as asymmetric catalysts in the epoxidation of unfunctionalized olefins. Up to 88% ee is obtained in the epoxidation of 1,2-dihydronaphthalene with one of these derivatives, 9, when a bulky imidazole ligand is used to block the unhindered face of the porphyrin catalyst.

引用

页码：692 / 703

页数：12

共 72 条

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