Asymmetric epoxidation of unfunctionalized alkenes with ammonium and phosphonium monopersulfates catalyzed by chiral Mn(III)-salen complexes

被引：24

作者：

Pietikäinen, P ^{[1
]}

机构：

[1] Univ Helsinki, Dept Chem, Organ Chem Lab, FIN-00014 Helsinki, Finland

来源：

TETRAHEDRON | 2000年 / 56卷 / 03期

关键词：

asymmetric reactions; epoxidations; catalysts;

D O I：

10.1016/S0040-4020(99)01008-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple cis-disubstituted and trisubstituted alkenes were enantioselectively epoxidized in mild conditions using various Mn(III)-salen complexes as catalysts and quaternary ammonium and phosphonium monopersulfates (Bu4NHSO5, Ph4PHSO5) as oxidants together with amine N-oxides as additives. The effect of the catalyst structure on the stereochemical outcome of the epoxidation reactions was studied. Generally, the 1,2-diphenylethylenediamine-derived complexes were found to give higher asymmetric induction compared to their 1,2-diaminocyclohexane-derived counterparts. Particularly high yields of epoxides (up to 98%) and good enantiomeric excesses (ee up to 93%) were obtained in the epoxidation of 2,2-dialkylchromenes and trisubstituted alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：417 / 424

页数：8

共 48 条

[1] ENANTIOSELECTIVE EPOXIDATION OF 2,2-DIMETHYL-2H-CHROMENES BY DIMETHYLDIOXIRANE AND JACOBSENS MN(III)SALEN CATALYSTS [J].

ADAM, W ;

JEKO, J ;

LEVAI, A ;

NEMES, C ;

PATONAY, T ;

SEBOK, P .

TETRAHEDRON LETTERS, 1995, 36 (21) :3669-3672

[2] HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS [J].

BRANDES, BD ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4378-4380

[3]

BRANDES BD, 1995, TETRAHEDRON LETT, V36, P5123

[4] OLEFIN EPOXIDATION AND ALKANE HYDROXYLATION CATALYZED BY ROBUST SULFONATED MANGANESE AND IRON PORPHYRINS SUPPORTED ON CATIONIC ION-EXCHANGE RESINS [J].

CAMPESTRINI, S ;

MEUNIER, B .

INORGANIC CHEMISTRY, 1992, 31 (11) :1999-2006

[5] Olefins epoxidation by Ph(4)PHSO(5) catalyzed by manganese porphyrins: A novel mechanistic proposal [J].

Campestrini, S ;

DiFuria, F ;

Ghiotti, P ;

Novello, F ;

Travaglini, C .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 105 (1-2) :17-23

[6] OXYGEN-TRANSFER FROM PH(4)PHSO(5) TO MANGANESE PORPHYRINS - KINETICS AND MECHANISM OF THE FORMATION OF THE OXO SPECIES IN HOMOGENEOUS SOLUTION [J].

CAMPESTRINI, S ;

DIFURIA, F ;

LABAT, G ;

NOVELLO, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (10) :2175-2180

[7] Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis [J].

Canali, L ;

Sherrington, DC .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (02) :85-93

[8] SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING 3'-THIOTHYMIDINE [J].

COSSTICK, R ;

VYLE, JS .

TETRAHEDRON LETTERS, 1989, 30 (35) :4693-4696

[9] Recent progress towards the understanding of metal-salen catalysed asymmetric alkene epoxidation [J].

Dalton, CT ;

Ryan, KM ;

Wall, VM ;

Bousquet, C ;

Gilheany, DG .

TOPICS IN CATALYSIS, 1998, 5 (1-4) :75-91

[10] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS [J].

DENG, L ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4320-4323

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