EFFECTS OF SECONDARY INTERACTIONS ON THE STEREOCHEMICAL OUTCOME OF RHODIUM(II) CARBOXYLATE CATALYZED CYCLOPROPANATION OF OLEFINS

被引:23
作者
DEMONCEAU, A
NOELS, AF
HUBERT, AJ
机构
[1] STATE UNIV LIEGE,MACROMOLEC CHEM & ORGAN CATALYSIS LAB,B-4000 LIEGE,BELGIUM
[2] STATE UNIV LIEGE,ORGAN SYNTH & CATALYSIS LAB,B-4000 LIEGE,BELGIUM
关键词
D O I
10.1016/S0040-4020(01)90524-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In cyclopropanation reactions of olefins catalysed by various dirhodium(II) tetracarboxylates, it is shown that besides the well-recognized electronic and steric effets, secondary interactions between the carbenoid complex and the substrate largely determine the stereoselectivity of the cyclopropanes. © 1990.
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页码:3889 / 3896
页数:8
相关论文
共 31 条
[1]   DIASTEREOSELECTIVITY IN THE SYNTHESIS OF 3(2H)-FURANONES - TOTAL SYNTHESIS OF (+)-MUSCARINE [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L .
TETRAHEDRON LETTERS, 1989, 30 (14) :1753-1756
[2]   TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].
ANCIAUX, AJ ;
HUBERT, AJ ;
NOELS, AF ;
PETINIOT, N ;
TEYSSIE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :695-702
[3]   TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .2. ADDITION TO AROMATIC-MOLECULES - CATALYSIS OF BUCHNER SYNTHESIS OF CYCLOHEPTATRIENES [J].
ANCIAUX, AJ ;
DEMONCEAU, A ;
NOELS, AF ;
HUBERT, AJ ;
WARIN, R ;
TEYSSIE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05) :873-876
[4]   STRUCTURE AND BONDING IN DIRHODIUM(II) TETRASALICYLATE [J].
BANCROFT, DP ;
COTTON, FA ;
HAN, S .
INORGANIC CHEMISTRY, 1984, 23 (16) :2408-2411
[5]   APPLICATIONS OF ORGANOMETALLIC REAGENTS IN BETA-LACTAM CHEMISTRY [J].
BARRETT, AGM ;
STURGESS, MA .
TETRAHEDRON, 1988, 44 (18) :5615-5652
[6]   RHODIUM(II)2,4,6-TRIARYLBENZOATES - IMPROVED CATALYSTS FOR THE SYN CYCLOPROPANATION OF Z-OLEFINS [J].
CALLOT, HJ ;
METZ, F .
TETRAHEDRON, 1985, 41 (20) :4495-4501
[7]   SYNTHESIS OF 4-ARYL-3,5-BIS(ALKOXYCARBONYL)-1,4-DIHYDROPYRAZINES [J].
CHORVAT, RJ ;
RORIG, KJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5779-5781
[8]   ATTEMPTED AND ACCOMPLISHED SYNTHESES OF A FEW MONOFLUORINATED CHRYSANTHEMIC ACID-DERIVATIVES [J].
COTTENS, S ;
SCHLOSSER, M .
TETRAHEDRON, 1988, 44 (23) :7127-7144
[9]   CATALYTIC FUNCTIONALIZATION OF ALKANES - EVIDENCE FOR ATTRACTIVE STERIC EFFECTS IN REACTIONS OF RHODIUM CARBENOIDS [J].
DEMONCEAU, A ;
NOELS, AF ;
HUBERT, AJ .
JOURNAL OF MOLECULAR CATALYSIS, 1989, 57 (02) :149-152
[10]  
DEMONCEAU A, 1984, B SOC CHIM BELG, V93, P949