Enantioselective copper-catalyzed cyclopropanation of silyl enol ethers

被引：30

作者：

Ebinger, A ^{[1
]}

Heinz, T ^{[1
]}

Umbricht, G ^{[1
]}

Pfaltz, A ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00499-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) complexes derived from semicorrins, azasemicorrins and bisoxazolines are efficient catalysts for the enantioselective cyclopropanation of silyl enol ethers with diazoacetates. The resulting cyclopropanes can be converted to gamma-ketocarboxylates by acid-induced ring cleavage. In this way methyl (2-oxocyclopentyl)- and (2-oxocyclohexyl)acetates have been prepared with up to 90 and 80% ee, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10469 / 10480

页数：12

共 48 条

[11] ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].

DOYLE, MP ;

AUSTIN, RE ;

BAILEY, AS ;

DWYER, MP ;

DYATKIN, AB ;

KALININ, AV ;

KWAN, MMY ;

LIRAS, S ;

OALMANN, CJ ;

PIETERS, RJ ;

PROTOPOPOVA, MN ;

RAAB, CE ;

ROOS, GHP ;

ZHOU, QL ;

MARTIN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775

[12]

DOYLE MP, 1996, ANGEW CHEM, V108, P1439

[13]

DOYLE MP, 1996, INT ED, V35, P133

[14] INTRAMOLECULAR MICHAEL ADDITION OF CHIRAL IMINES TO ENOATES - A NEW ASYMMETRIC CARBOCYCLIZATION REACTION [J].

DUMAS, F ;

DANGELO, J .

TETRAHEDRON-ASYMMETRY, 1990, 1 (03) :167-170

[15]

EBINGER A, 1998, THESIS U BASEL

[16]

Evans D. A., 1992, ANGEW CHEM, V104, P439

[17] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728

[18] BIS(OXAZOLINE) AS LIGANDS FOR SELF-ASSEMBLING CHIRAL COORDINATION POLYMERS - STRUCTURE OF A COPPER(I) CATALYST FOR THE ENANTIOSELECTIVE CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

SCOTT, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (04) :430-432

[19] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .1. SYNTHESIS OF CHIRAL SEMICORRIN LIGANDS AND GENERAL CONCEPTS [J].

FRITSCHI, H ;

LEUTENEGGER, U ;

SIEGMANN, K ;

PFALTZ, A ;

KELLER, W ;

KRATKY, C .

HELVETICA CHIMICA ACTA, 1988, 71 (06) :1541-1552

[20] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .2. ENANTIOSELECTIVE CYCLOPROPANE FORMATION FROM OLEFINS WITH DIAZO-COMPOUNDS CATALYZED BY CHIRAL (SEMICORRINATO)COPPER COMPLEXES [J].

FRITSCHI, H ;

LEUTENEGGER, U ;

PFALTZ, A .

HELVETICA CHIMICA ACTA, 1988, 71 (06) :1553-1565

← 1 2 3 4 5 →