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Titolo:
DESIGN AND SYNTHESIS OF OPTICALLY-ACTIVE MANGANESE(III) COMPLEX CATALYSTS FOR ENANTIOSELECTIVE EPOXIDATION USING MOLECULAR-OXYGEN
Autore:
YAMADA T; NAGATA T; MUKAIYAMA T;
Indirizzi:
MITSUI PETROCHEM IND CO LTD,BASIC RES LABS ORGAN SYNTHESIS SODEGAURA CHIBA 29902 JAPAN SCI UNIV TOKYO,FAC SCI,DEPT APPL CHEM,SHINJUKU KU TOKYO 162 JAPAN
Titolo Testata:
Nippon kagaku kaishi
fascicolo: 10, , anno: 1995,
pagine: 755 - 762
SICI:
0369-4577(1995):10<755:DASOOM>2.0.ZU;2-E
Fonte:
ISI
Lingua:
JPN
Soggetto:
ASYMMETRIC EPOXIDATION; UNFUNCTIONALIZED OLEFINS; NICKEL(II) COMPLEXES; AEROBIC EPOXIDATION; IRON COMPLEXES; DERIVATIVES; ALDEHYDE; PORPHYRINS; OXIDATION; ALCOHOL;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
39
Recensione:
Indirizzi per estratti:
Citazione:
T. Yamada et al., "DESIGN AND SYNTHESIS OF OPTICALLY-ACTIVE MANGANESE(III) COMPLEX CATALYSTS FOR ENANTIOSELECTIVE EPOXIDATION USING MOLECULAR-OXYGEN", Nippon kagaku kaishi, (10), 1995, pp. 755-762

Abstract

Epoxidation of olefins by molecular oxygen was developed by combiningaldehyde with a catalytic amount of nickel(II), iron(III), vanadium(IV), and manganese(II) complexes containing 1,3-diketona- to ligands. The efficiency of catalysts was improved by designing the structure of the ligands, and various olefins, styrene derivatives, and cr,P-unsaturated carboxamides were oxidized to the corresponding epoxides in highyields. It was also revealed that the stereofacial selection of cholesteryl derivatives in the aerobic epoxidation was different from that of the conventional epoxidation using peroxy acids, such as mCPBA or peracetic acid. Novel manganese(III) complexes having optically active 1,3-diketo-type ligands, N,N-bis (3-oxobutyhdene) diamine derivatives,were designed and synthesized on the basis of the characterization ofX-ray analysis. In the presence of a catalytic amount of these manganese(III) complexes, enantioselective and aerobic epoxidations of unfunctionalized olefins were achieved by the combined use of molecular oxygen and pivalaldehyde, and the corresponding optically active epoxideswere obtained with good-to-high enantiomeric excess. It was found that the absolute configuration of the resulting epoxides was reversed bythe addition of N-methylimidazole. Based on these observations, the key intermediates in the present aerobic epoxidation were tentatively proposed to be acylperoxomanganese complexes.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 21/09/20 alle ore 12:49:46