Synthesis, characterization and reactions of enantiomerically pure 'winged' spirane porphyrazines

被引：13

作者：

Hachiya, S

Cook, AS

Williams, DBG

Montalban, AG

Barrett, AGM ^{[1
]}

Hoffman, BM

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

[2] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 35期

基金：

美国国家科学基金会; 英国工程与自然科学研究理事会;

关键词：

porphyrins and analogs; complexes; epoxidation; asymmetric induction;

D O I：

10.1016/S0040-4020(00)00607-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from L-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6565 / 6569

页数：5

相关论文

共 27 条

[1]

[Anonymous], 1978, Top. Stereochem

[2] INVESTIGATION ON FACTORS RULING CATALYTIC EFFICIENCY AND CHEMICAL-STABILITY OF MN(III) PORPHYRINS IN HOCL OLEFIN EPOXIDATION - CONDITIONS FOR PRACTICAL APPLICATION [J].

BANFI, S ;

MONTANARI, F ;

QUICI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1850-1859

[3] solitaire-porphyrazines: Synthetic, structural, and spectroscopic investigation of complexes of the novel binucleating norphthalocyanine-2,3-dithiolato ligand [J].

Baumann, TF ;

Nasir, MS ;

Sibert, JW ;

White, AJP ;

Olmstead, MM ;

Williams, DJ ;

Barrett, AGM ;

Hoffman, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10479-10486

[4] Porphyrazinediols: Synthesis, characterization, and complexation to group IVB metallocenes [J].

Bellec, N ;

Montalban, AG ;

Williams, DBG ;

Cook, AS ;

Anderson, ME ;

Feng, XD ;

Barrett, AGM ;

Hoffman, BM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1774-1779

[5] PHOTOSENSITIZERS OF THE PORPHYRIN AND PHTHALOCYANINE SERIES FOR PHOTODYNAMIC THERAPY [J].

BONNETT, R .

CHEMICAL SOCIETY REVIEWS, 1995, 24 (01) :19-33

[6] MANGANESE PORPHYRIN COMPLEXES [J].

BOUCHER, LJ .

COORDINATION CHEMISTRY REVIEWS, 1972, 7 (03) :289-&

[7] THREITOL-STRAPPED MANGANESE PORPHYRINS AS ENANTIOSELECTIVE EPOXIDATION CATALYSTS OF UNFUNCTIONALIZED OLEFINS [J].

COLLMAN, JP ;

LEE, VJ ;

KELLENYUEN, CJ ;

ZHANG, XM ;

IBERS, JA ;

BRAUMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) :692-703

[8] Enantiomerically pure ''winged'' spirane porphyrazinoctaols [J].

Cook, AS ;

Williams, DBG ;

White, AJP ;

Williams, DJ ;

Lange, SJ ;

Barrett, AGM ;

Hoffman, BM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07) :760-761

[9] PORPHYRINS WITH APPENDED PHENANTHROLINE UNITS - A MEANS BY WHICH PORPHYRIN PI-SYSTEMS CAN BE CONNECTED TO AN EXTERNAL REDOX CENTER [J].

CROSSLEY, MJ ;

BURN, PL ;

LANGFORD, SJ ;

PRASHAR, JK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1921-1923

[10] Metalloporphyrins as ligands: Synthesis and characterization of [(eta(6)-cymene)-Ru{eta(5)-Ni(OEP)}](2+) [J].

Dailey, KK ;

Yap, GPA ;

Rheingold, AL ;

Rauchfuss, TB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16) :1833-1835