Syntheses of nonracemic ortho-mercurated and ortho-ruthenated complexes of 2-[tricarbonyl(η6-phenyl)chromium]pyridine

被引:43
作者
Djukic, JP
Berger, A
Duquenne, M
Pfeffer, M
de Cian, A
Kyritsakas-Gruber, N
Vachon, J
Lacour, J
机构
[1] Univ Strasbourg, CNRS, UMR 7513, F-67000 Strasbourg, France
[2] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1021/om0494667
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of racemic orthomercurated (eta(6)-arene)tricarbonylchromium complexes with bis [(eta(6) -eymene)ruthenium(II)dichloride] affords the corresponding dinuclear (Cr,Ru) products with moderate yields, which have been satisfactorily characterized by X-ray diffraction analysis. The synthesis of nonracemic orthomercurated (eta(6) -arene)tricarbonylchromium complexes has been attempted starting from enantio-enriched homo- and heteroleptic Pd-(II) bischelated complexes. Both enantiomers of ortho-mercurated 2-[tricarbonyl( eta(6) -phenyl)chromium] pyridine have been synthesized by reaction of a heteroleptic Pd(II) bischelated with HgCl2. The two mercury(II) complexes were also submitted to a transmetalation reaction with bis [(eta(6) -cymene)ruthenium(II)dichloride] and yielded the corresponding nonracemic (Cr, Ru) products, with enantiomeric excesses ranging from 82 to 89% as suggested by H-1 NMR analyses in the presence of BINPHAT anion.
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页码:5757 / 5767
页数:11
相关论文
共 81 条
[1]   CARBON-CARBON AND CARBON-NITROGEN BOND FORMATION MEDIATED BY RUTHENIUM(II) COMPLEXES - SYNTHESIS OF (1H)-ISOQUINOLINIUM DERIVATIVES [J].
ABBENHUIS, HCL ;
PFEFFER, M ;
SUTTER, JP ;
DECIAN, A ;
FISCHER, J ;
JI, HL ;
NELSON, JH .
ORGANOMETALLICS, 1993, 12 (11) :4464-4472
[2]   Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].
Anderson, CE ;
Overman, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413
[3]   The asymmetric synthesis of phosphorus- and sulfur-containing tricarbonyl(η6-arene)chromium complexes using the chiral base approach [J].
Ariffin, A ;
Blake, AJ ;
Ewin, RA ;
Li, WS ;
Simpkins, NS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (21) :3177-3189
[4]  
Ariffin A, 1997, SYNLETT, P1453
[5]   Use of a bis-lithium amide base in asymmetric metallation of tricarbonyl(η6-1,3-dihydroisobenzothiophene)chromium(0) [J].
Ariffin, A ;
Blake, AJ ;
Ewin, RA ;
Simpkins, NS .
TETRAHEDRON-ASYMMETRY, 1998, 9 (15) :2563-2566
[6]   METALLACYCLES WITH STEREOGENIC METAL CENTERS - SYNTHESIS AND CHARACTERIZATION OF DIASTEREOMERIC CYCLORUTHENATED CHIRAL AMINES [J].
ATTAR, S ;
NELSON, JH ;
FISCHER, J ;
DECIAN, A ;
SUTTER, JP ;
PFEFFER, M .
ORGANOMETALLICS, 1995, 14 (10) :4559-4569
[7]   ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES [J].
AUBE, J ;
HEPPERT, JA ;
MILLIGAN, ML ;
SMITH, MJ ;
ZENK, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3563-3570
[8]   ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].
BENNETT, MA ;
SMITH, AK .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241
[9]   Chloride-promoted synthesis of cis bis-chelated palladium(II) complexes from ortho-mercurated tricarbonyl(η6-arene)chromium complexes [J].
Berger, A ;
Djukic, JP ;
Pfeffer, M ;
Lacour, J ;
Vial, L ;
de Cian, A ;
Kyritsakas-Gruber, N .
ORGANOMETALLICS, 2003, 22 (25) :5243-5260
[10]   Novel heteroleptic cis-(C N)2Pd(II) chelates for the preparation of enantiopure planar chiral cyclopalladated 2-[tricarbonyl(η6-phenyl)chromium]pyridine [J].
Berger, A ;
Djukic, JP ;
Pfeffer, M ;
de Cian, A ;
Kyritsakas-Gruber, N ;
Lacour, J ;
Vial, L .
CHEMICAL COMMUNICATIONS, 2003, (05) :658-659