Cyclopropanation of alkenes with ethyl diazoacetate catalysed by ruthenium porphyrin complexes

被引:88
作者
Galardon, E [1 ]
LeMaux, P [1 ]
Simonneaux, G [1 ]
机构
[1] UNIV RENNES 1,CNRS,LAB CHIM ORGANOMET & BIOL,F-35042 RENNES,FRANCE
关键词
D O I
10.1039/a700098g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ruthenium porphyrin complexes are active catalysts for the cyclopropanation of styrene derivatives by ethyl diazoacetate with good to very good diastereoselectivity; moderate enantiomeric excesses (34%) are observed using a chiral porphyrin as catalyst.
引用
收藏
页码:927 / 928
页数:2
相关论文
共 15 条
[1]   SPECTROSCOPIC AND STRUCTURAL CHARACTERIZATION OF RUTHENIUM(II) CARBONYL-PORPHINE COMPLEXES [J].
BONNET, JJ ;
EATON, SS ;
EATON, GR ;
HOLM, RH ;
IBERS, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2141-2149
[2]   STERICALLY CROWDED CYCLOPROPANATION CATALYSTS - SYN-SELECTIVITY USING RHODIUM(III)PORPHYRINS [J].
CALLOT, HJ ;
METZ, F ;
PIECHOCKI, C .
TETRAHEDRON, 1982, 38 (15) :2365-2369
[3]   CLEAVAGE OF RUTHENIUM AND OSMIUM PORPHYRIN DIMERS - FORMATION OF ORGANOMETALLIC RUTHENIUM PORPHYRIN COMPLEXES AND HIGHLY REDUCED METALLOPORPHYRIN SPECIES [J].
COLLMAN, JP ;
BROTHERS, PJ ;
MCELWEEWHITE, L ;
ROSE, E ;
WRIGHT, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4570-4571
[4]   REACTIVITY OF RUTHENIUM 5,10,15,20-TETRAMESITYLPORPHYRIN TOWARDS DIAZOESTERS - FORMATION OF OLEFINS [J].
COLLMAN, JP ;
ROSE, E ;
VENBURG, GD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (11) :934-935
[5]   MODELS OF OXIDIZED HEME-PROTEINS - PREPARATION AND CHARACTERIZATION OF A TRANS-DIOXORUTHENIUM(VI) PORPHYRIN COMPLEX [J].
GROVES, JT ;
QUINN, R .
INORGANIC CHEMISTRY, 1984, 23 (24) :3844-3846
[6]   PREPARATION, CHARACTERIZATION AND REACTION OF THE FIRST DIOXORUTHENIUM(VI) COMPLEXES OF CHIRAL PICKET-FENCE PORPHYRINS [J].
LEMAUX, P ;
BAHRI, H ;
SIMONNEAUX, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) :1287-1288
[7]   SHAPE-SELECTIVE AND ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY RHODIUM PORPHYRINS [J].
MAXWELL, JL ;
OMALLEY, S ;
BROWN, KC ;
KODADEK, T .
ORGANOMETALLICS, 1992, 11 (02) :645-652
[8]   HIGHLY ENANTIOSELECTIVE SYNTHESIS OF CYCLOPROPANE DERIVATIVES THROUGH CHIRAL COBALT(II) COMPLEX CATALYZED CARBENOID REACTION - GENERAL SCOPE AND FACTORS DETERMINING ENANTIOSELECTIVITY [J].
NAKAMURA, A ;
KONISHI, A ;
TATSUNO, Y ;
OTSUKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3443-3448
[9]   NEW CHIRAL RUTHENIUM BIS(OXAZOLINYL)PYRIDINE CATALYST - EFFICIENT ASYMMETRIC CYCLOPROPANATION OF OLEFINS WITH DIAZOACETATES [J].
NISHIYAMA, H ;
ITOH, Y ;
MATSUMOTO, H ;
PARK, SB ;
ITOH, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2223-2224
[10]   ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY A RHODIUM CHIRAL FORTRESS PORPHYRIN [J].
OMALLEY, S ;
KODADEK, T .
ORGANOMETALLICS, 1992, 11 (06) :2299-2302