What is the origin of highly asymmetric induction by a chiral (salen)manganese(III) complex? Design of a conformationally fixed complex and its application to asymmetric epoxidation of 2,2-dimethylchromenes

被引：55

作者：

Ito, YN ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(98)00763-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The optically active (salen)manganese(III) complex 1 having a carboxylate group on the ethylenediamine moiety was found to be an efficient catalyst for the asymmetric epoxidation of several 2,2-dimethylchromene derivatives (up to 99% ee). A high level of turn-over number (up to 9, 200) was also achieved in this epoxidation. The pseudo-axially oriented carboxylate in 1 was postulated to coordinate to the manganese ion and to fix the conformation of the salen ligand in the form enantiomeric to that of normal chiral (salen)manganese(III) complexes. This was supported by the absolute configurations of the produced epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4325 / 4328

页数：4

共 39 条

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[32] N-ALKYL IMIDAZOLES AS EFFECTIVE AXIAL LIGANDS IN THE AEROBIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS CATALYZED BY OPTICALLY-ACTIVE MANGANESE(III)-SALEN-TYPE COMPLEX
IMAGAWA, K
NAGATA, T
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CHEMISTRY LETTERS, 1994, (03) : 527 - 530
[33] Asymmetric epoxidation of alkenes with tert-butyl hydroperoxide catalyzed by a novel chiral complex of manganese(III) containing a sugar based tridentate Schiff-base ligand
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CATALYSIS COMMUNICATIONS, 2007, 8 (09) : 1345 - 1348
[34] Cu2+-templated self-assembly of an asymmetric Salen-Cu(II) complex and its application in catalytic polymerization of methyl methacrylate (MMA)
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INORGANIC CHEMISTRY COMMUNICATIONS, 2014, 44 : 173 - 176
[35] Catalytic asymmetric epoxidation of unfunctionalized olefins using a series novel type of layered crystalline organic polymer-inorganic hybrid zinc phosphonate-phosphate immobilized aryldiamine modified chiral salen Mn(III) complex
Huang, Jing
Fu, Xiangkai
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APPLIED CATALYSIS A-GENERAL, 2011, 407 (1-2) : 163 - 172
[36] RETRACTED: Synthesis of a novel type of chiral salen Mn(III) complex immobilized on crystalline zinc poly(styrene-phenylvinylphosphonate)-phosphate (ZnPS-PVPP) as effective catalysts for asymmetric epoxidation of unfunctionalized olefins (Retracted Article)
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CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (08) : 1472 - 1482
[37] A VERY MILD, CATALYTIC AND VERSATILE PROCEDURE FOR ALPHA-OXIDATION OF KETONE SILYL ENOL ETHERS USING (SALEN)MANGANESE(III) COMPLEXES - A NEW, CHIRAL COMPLEX GIVING ASYMMETRIC INDUCTION - A POSSIBLE MODEL FOR SELECTIVE BIOCHEMICAL OXIDATIVE REACTIONS THROUGH ENOL FORMATION
REDDY, DR
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JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (02) : 172 - 173
[38] RETRACTION: Synthesis of a novel type of chiral salen Mn(iii) complex immobilized on crystalline zinc poly(styrene-phenylvinylphosphonate)-phosphate (ZnPS-PVPP) as effective catalysts for asymmetric epoxidation of unfunctionalized olefins (Retraction of Vol 1, Pg 1472, 2011)
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Fu, Xiangkai
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CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (11) : 3931 - 3931
[39] Catalytic asymmetric epoxidation of unfunctionalized olefins using a series novel type of layered crystalline organic polymer-inorganic hybrid zinc phosphonate-phosphate immobilized aryldiamine modified chiral salen Mn (III) complex (vol 407, pg 163, 2011)
Huang, Jing
Fu, Xiangkai
Miao, Qiang
APPLIED CATALYSIS A-GENERAL, 2012, 419 : 221 - 221

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