Applications of optically active metallacycles: new userful materials for the determination of the enantiomeric excess of Lewis bases and as resolving agents for monodentate phosphines

EnglishThe synthesis of new optically active cyclopalladated derivatives containing imines and primary amines is described as well as their applications for the determination of the enantiomeric excess and as resolving agents of Lewis bases. The synthesis and resolution of new monodentate P-chiral tertiary phosphines is also reported, as well as the application of these new ligands to asymmetric catalysis. Besides this, some chiral secondary phosphines have been prepared and their configurational stability has been studied catalaEs descriu la sintesi de nous compostos ciclopal·ladats derivats d'imines i amines primaries, opticament actius, aixi com les seves aplicacions per a la determinacio de l'exces enantiomeric i per a la resolucio de bases de Lewis. Tambe es comenta la sintesi i resolucio de noves fosfines P-quirals, aixi com la seva aplicacio a processos de catalisi asimetrica. A mes, es descriu la preparacio d'algunes fosfines secundaries quirals i s'estudia la seva estabilitat configuracional.

[1]  P. Valerga,et al.  RESOLUTION OF BENZYLCYCLOHEXYLPHENYLPHOSPHINE BY PALLADIUM(II)-AMINE METALLACYCLES. A NEW LIGAND FOR ASYMMETRIC HYDROVINYLATION , 1999 .

[2]  P. Leung,et al.  A VERSATILE AND EFFICIENT APPROACH TO ENANTIOMERICALLY PURE MONODENTATE AND BIDENTATE P-CHIRAL PHOSPHINES , 1999 .

[3]  W. Keim,et al.  Asymmetric hydrovinylation of styrene applying cationic allyl palladium complexes of a P-chiral ligand , 1998 .

[4]  S. Wild Resolutions of tertiary phosphines and arsines with orthometallated palladium (II)—amine complexes , 1997 .

[5]  P. Valerga,et al.  An Approach to the Synthesis of Platinum Complexes Containing Chiral Monodentate Phosphines with Simultaneous Regeneration of the Resolving Agent , 1997 .

[6]  Montserrat Gómez,et al.  Variable-Temperature and -Pressure Kinetics and Mechanism of the Cyclopalladation Reaction of Imines in Aprotic Solvent , 1997 .

[7]  J. Albert,et al.  Cyclopalladation of the primary amine (R)-(+)-1-(1-naphthyl)ethylamine: a new resolving agent for monodentate phosphines , 1997 .

[8]  A. Crispini,et al.  Five-membered cyclopalladated rings: Cambridge structural database analysis of geometrical parameters and ‘aromatic’ character , 1997 .

[9]  A. Willis,et al.  First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex. , 1996, Inorganic chemistry.

[10]  V. V. Dunina,et al.  A resolution of monodentate P∗ chiral phosphine , 1995 .

[11]  J. Sales,et al.  Optically Active Exocyclic Cyclopalladated Derivatives of Benzylidene-(R)-(1-phenylethyl)amines: Syntheses and X-ray Molecular Structures of [Pd(2-{(E)-(R)-CHMeN:CH-2',6'-Cl2C6H3}C6H4)Cl(PPh3)] and [Pd(2-{(Z)-(R)-CHMeN:CH-2',6'-F2C6H3}C6H4)I(PPh3)] , 1995 .

[12]  G. Muller,et al.  CHIRAL CYCLOPALLADATED COMPOUNDS FOR ENANTIOMERIC PURITIES OF FUNCTIONALIZED PHOSPHINES BY MEANS OF MULTINUCLEAR NMR , 1995 .

[13]  John M. Brown,et al.  Contrasting behaviour of related palladium complex-derived resolving agents. 8-H conformational locking of the 1-naphthyl side-chain , 1995 .

[14]  G. Salem,et al.  Stereochemistry and Stability of Free and Coordinated Secondary Phosphines. Crystal and Molecular Structure of [S-[(R*,R*),(R*)]]-(+)589-[PtCl{1,2-C6H4(PMePh)2}(PHMePh)]PF6.cntdot.CH2Cl2 , 1995 .

[15]  M. Zabłocka,et al.  Preparation of Scalemic P-Chiral Phosphines and Their Derivatives. , 1994 .

[16]  M. Zabłocka,et al.  Preparation of Scalemic P-Chiral Phosphines and Their Derivatives , 1994 .

[17]  R. Noyori,et al.  Asymmetric catalysis in organic synthesis , 1994 .

[18]  W. Mcfarlane,et al.  Chiral ligands: unambiguous assignment of absolute configuration by NMR spectroscopy , 1993 .

[19]  J. Vicente,et al.  Orthometallated primary amines. Part 1. Facile preparation of the first optically active cyclopalladated primary amines , 1993 .

[20]  P. Leung,et al.  Versatile chiral palladium(II) complexes for enantiomeric purities of 1,2-diamines , 1992 .

[21]  H. R. Sonawane,et al.  Recent developments in the synthesis of optically active α-arylpropanoic acids: An important class of non-steroidal anti-inflammatory agents☆ , 1992 .

[22]  V. M. Potapov,et al.  General Principles and Characteristics of Cyclopalladation Reactions , 1988 .

[23]  W. Ollis,et al.  Comprehensive organic chemistry : the synthesis and reactions of organic compounds , 1978 .

[24]  S. Trofimenko SOME STUDIES OF THE CYCLOPALLADATION REACTION , 1973 .