Conversion of D-penicillaminato trinuclear to mononuclear palladium(II) structure by diamine ligands: remarkable enantioselectivity toward racemic 1,2-cyclohexanediamine.

The reactions of an S-bridged trinuclear palladium(II) complex, [Pd(3)(D-pen-N,O,S)(3)] (D-H(2)pen = D-penicillamine), with ethylenediamine (en) and racemic (R,R/S,S) 1,2-cyclohexanediamine (chxn) in water gave mononuclear palladium(II) complexes, [Pd(D-pen-N,S)(en)] (1) and [Pd(D-pen-N,S)(chxn)] (2), respectively. Of two diastereomers, [Pd(D-pen-N,S)(R,R-chxn)] (2(R)) and [Pd(D-pen-N,S)(S,S-chxn)] (2(S)), possible for 2, 2(S) was exclusively isolated in a high yield.

[1]  T. Konno,et al.  Enantioselective/anion-selective incorporation of tris(ethylenediamine) complexes into 2D coordination spaces between tripalladium(II) supramolecular layers with D-penicillaminate. , 2011, Inorganic chemistry.

[2]  N. Yoshinari,et al.  A multinuclear coordination system of L-cysteine and L-penicillamine that induce opposite chiralities at metal centers. , 2009, Angewandte Chemie.

[3]  N. Yoshinari,et al.  Reversible Conversion of Tetranuclear, Trinuclear, and Mononuclear Palladium(II) Complexes with D-Penicillaminate , 2009 .

[4]  N. Yoshinari,et al.  Drastic Change in Dimensional Structures of D-Penicillaminato (AuI2PtII2ZnII)n Coordination Polymers by Moderate Change in Solution pH , 2009 .

[5]  S. Kawauchi,et al.  Axial chirality control of tropos BIPHEP-Rh complexes by chiral dienes: synergy effect in catalytic asymmetric hydrogenation. , 2008, Chemical communications.

[6]  M. Reetz Combinatorial transition-metal catalysis: mixing monodentate ligands to control enantio-, diastereo-, and regioselectivity. , 2008, Angewandte Chemie.

[7]  T. Konno,et al.  A nickel(II) gold(I) D-penicillaminate coordination system with multiple switching in color, magnetism, and chirality. , 2007, Angewandte Chemie.

[8]  T. Konno,et al.  A Novel S-bridged PdII2HgII Metallacycle of D-Penicillaminate that Forms a Unique Supramolecular Structure Combined with Tetraamminepalladium(II) , 2007 .

[9]  K. Mikami,et al.  Enantiodiscrimination and enantiocontrol of neutral and cationic PtII complexes bearing the tropos biphep ligand: application to asymmetric lewis acid catalysis. , 2005, Angewandte Chemie.

[10]  T. Konno,et al.  A rock-salt-like lattice structure consisting of monocationic and monoanionic AuIAgICuII supramolecular cages of D-penicillaminate. , 2005, Angewandte Chemie.

[11]  A. J. Blake,et al.  Pinwheel motifs: formation of unusual homo- and hetero-nuclear aggregates via bridging thiolates. , 2003, Chemical communications.

[12]  J. Nedeljković,et al.  Influence of sodium dodecyl sulfate on the kinetics of complex formation between [PdCl(dien)]+ and sulfur containing ligands l-cysteine and glutathione , 2003 .

[13]  K. Mikami,et al.  Asymmetric activation of the Pd catalyst bearing the tropos biphenylphosphine (BIPHEP) ligand with the chiral diaminobinaphthyl (DABN) activator. , 2002, Organic letters.

[14]  A. Stash,et al.  Palladium Clusters Pd4(SEt)4(OAc)4and Pd6(SEt)12: Structure and Properties , 2001 .

[15]  P. White,et al.  Diastereoisomer Interconversion in Chiral BiphepPtX2 Complexes , 2000 .

[16]  K. Mikami,et al.  Enantiomer-selective activation of racemic catalysts. , 2000, Accounts of chemical research.

[17]  T. Konno,et al.  Stereoselectivity for S-Bridged Polynuclear Transition Metal Complexes Formed by Aggregation of Octahedral Complexes to Square-Planar Palladium(II) , 1999 .

[18]  A. Willis,et al.  Self-Assembly of Homochiral Double Helix and Side-by-Side Helix Conformers of Double-Stranded Disilver(I)- and Digold(I)-Tetra(tertiary phosphine) Helicates. , 1997, Inorganic chemistry.

[19]  G. Salem,et al.  Synthesis, resolution and reactions of (±)-(2-aminophenyl)methylphenylphosphine. Crystal and molecular structure of (R*,R*, S*, R*)-(±)-(1,3-bis{[2-(methylphenylphosphino)phenyl]amino}propane)nickel(II) perchlorate , 1995 .

[20]  G. Salem,et al.  Synthesis, resolution and reactions of (±)-1-(dimethylarsino)-2-(methylphenylphosphino)benzene. Crystal and molecular structure of [(S), (S)]-(+)589-{2-[1-(dimethylamino)ethyl]phenyl-C1,N}[1-(dimethylarsino)-2-(methylphenylphosphino)benzene-As,P]palladium(II) hexafluorophosphate , 1995 .

[21]  P. Leung,et al.  Stereochemical Investigation of Bis(bidentate)-Palladium(II) Complexes. Transmission of Ring Chiralities between Chelating Amine Ligands via Their Prochiral N-Methyl Substituents , 1994 .

[22]  T. Konno,et al.  A New Class of S-Bridged Hexanuclear Complexes with Aminoethanethiolate Ligands. Formation and Structural Characterization of [PdII2{NiII(aet)2}x{PdII(aet)2}4-x]Br4 (x = 0-4; aet = 2-Aminoethanethiolate) , 1994 .

[23]  G. Salem,et al.  Optically active asymmetric bidentate ligands. Crystal and molecular structure of {(R), (S)-(–)589-2-[1-(dimethylamino)ethyl]phenyl-C2,N}[1-(diphenylphosphino)-2-(methylphenylphosphino) benzene-P,P′]palladium(II) hexafluorophosphate , 1993 .

[24]  S. Wild,et al.  Metal complexes containing diastereoisomers and enantiomers of o-phenylenebis(methylphenylarsine) and its phosphorus analog. 1. Stereochemistry and dynamic behavior of square-planar and square-pyramidal complexes of bivalent nickel , 1981 .

[25]  S. Wild,et al.  Metal complexes containing Diastereoisomers and Enantiomers of o -Phenylenebis(methylphenylarsine) and its Phosphorous Analogue. 2. Stereochemistry and Dynamic Behaviour of Square-Planar and Square-Pyramidal Complexes of Bivalent Palladium and Platinum , 1981 .

[26]  R. Hay,et al.  Hydrolysis of α-amino-acid esters in mixed-ligand complexes with ethylenediaminepalladium(II) , 1981 .