CHIRAL RECOGNITION IN PLATINUM COMPLEXES OF 1,2-DIPHENYL-N,N'-BIS[(2,4,6-TRIMETHYLPHENYL)METHYL]-1,2-DIAMINOETHANE - STEREOSELECTIVE COORDINATION OF OLEFINS AND MOLECULAR-STRUCTURE OF A TRIGONAL BIPYRAMIDAL ADDUCT

被引:8
作者
CUCCIOLITO, ME
JAMA, MA
GIORDANO, F
VITAGLIANO, A
DEFELICE, V
机构
[1] UNIV NAPLES FEDERICO II,DIPARTIMENTO CHIM,I-80134 NAPLES,ITALY
[2] UNIV MOLISE,FAC AGR,I-86100 CAMPBOBASSO,ITALY
关键词
D O I
10.1021/om00003a016
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Trigonal bipyramidal olefin-platinum complexes of the title chiral diamine (mestien) have been synthetized and their stereochemistry has been investigated by H-1 and C-13 NMR spectroscopy. The molecular structure of the complex PtClMe ((E)-ClCH = CHCl) (mestien) has been determined by X-ray diffraction analysis. The coordinated nitrogen atoms display a single configuration, and a high enantioface selectivity is observed in the coordination of prochiral olefins having a moderate lateral bulk. The selectivity can be correlated to the conformation adopted by the diamine ligand, which shows a remarkable similarity to those calculated for a proposed intermediate in the enantioselective dihydroxylation of olefins by osmium tetraoxide.
引用
收藏
页码:1152 / 1160
页数:9
相关论文
共 19 条
[1]   5-COORDINATE ALKENE COMPLEXES OF PALLADIUM(II) AND PLATINUM(II) [J].
ALBANO, VG ;
NATILE, G ;
PANUNZI, A .
COORDINATION CHEMISTRY REVIEWS, 1994, 133 :67-114
[2]   5-COORDINATE OLEFIN COMPLEXES OF PLATINUM(II) CONTAINING OMEGA-BONDED CARBON LIGANDS - SYNTHESIS AND CHARACTERIZATION OF [PTCLME(ETA-2-C2H4)(N-N')] COMPLEXES - MOLECULAR-STRUCTURE OF AN ADDUCT WITH A CHIRAL METAL CENTER AND OF ITS PARENT 4-COORDINATE COMPLEX [J].
ALBANO, VG ;
BRAGA, D ;
DEFELICE, V ;
PANUNZI, A ;
VITAGLIANO, A .
ORGANOMETALLICS, 1987, 6 (03) :517-525
[3]   5-COORDINATION VS 4-COORDINATION IN PLATINUM(II) - OLEFIN COMPLEXES WITH BIDENTATE NITROGEN LIGANDS [J].
ALBANO, VG ;
DEMARTIN, F ;
DERENZI, A ;
MORELLI, G ;
SAPORITO, A .
INORGANIC CHEMISTRY, 1985, 24 (13) :2032-2039
[4]   ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].
COREY, EJ ;
JARDINE, PD ;
VIRGIL, S ;
YUEN, PW ;
CONNELL, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244
[5]   5-COORDINATE OLEFIN COMPLEXES OF PLATINUM(II) CONTAINING SIGMA-BONDED CARBON LIGANDS - COORDINATION ENVIRONMENT AND STABILITY [J].
CUCCIOLITO, ME ;
DEFELICE, V ;
PANUNZI, A ;
VITAGLIANO, A .
ORGANOMETALLICS, 1989, 8 (05) :1180-1187
[6]   RESOLUTION OF ALLYLIC ALCOHOLS VIA COPPER(I) COMPLEXES WITH A CHIRAL DIAMINE [J].
CUCCIOLITO, ME ;
RUFFO, F ;
VITAGLIANO, A ;
FUNICELLO, M .
TETRAHEDRON LETTERS, 1994, 35 (01) :169-170
[7]   SYNTHESIS, STRUCTURE, AND STEREOCHEMISTRY OF 5-COORDINATE PLATINUM(II)-OLEFIN COMPLEXES WITH A CHIRAL DIAMINE [J].
DERENZI, A ;
DIBLASIO, B ;
SAPORITO, A ;
SCALONE, M ;
VITAGLIANO, A .
INORGANIC CHEMISTRY, 1980, 19 (04) :960-966
[8]   RAPID INVERSION VERSUS STABLE CHIRAL CENTER FORMATION - DIFFERENT BEHAVIOR OF COORDINATED NITROGENS IN 4-COORDINATE AND 5-COORDINATE PLATINUM(II) COMPLEXES WITH N,N'-DISUBSTITUTED ETHYLENEDIAMINES [J].
FANIZZI, FP ;
MARESCA, L ;
NATILE, G ;
LANFRANCHI, M ;
MANOTTILANFREDI, AM ;
TIRIPICCHIO, A .
INORGANIC CHEMISTRY, 1988, 27 (14) :2422-2431
[9]  
Frenz B. A., 1982, STRUCTURE DETERMINAT
[10]  
JORGENSEN KA, 1990, CHEM REV, V90, P1483