Borane and Platinum Complexes
Letters in Organic Chemistry, 2010, Vol. 7, No. 3
239
[
18]
Kunze, C.; Selent, D.; Neda, I.; Freytag, M.; Jones, P.G.;
Schmutzler, R.; Baumann, W.; Börner, A. Calix[4]arene-based bis-
phosphonites, bis-phosphites, and bis-O-acyl-phosphites as ligands
in the rhodium(I)-catalyzed hydroformylation of 1-octene. Z.
Anorg. Allg. Chem. 2002, 628, 779-787.
Matos, R.M.; da Costa, R.F.F.; Knupp, W.F.; Silva, J.A.D.; Passos,
B.F.T. Syntheses and P-31 NMR studies of transition metal
complexes containing derivatives of dioxaphospholane and
dioxaphosphorinane. J. Braz. Chem. Soc. 2000, 11, 311-316.
Mariz, R.; Briceño, A.; Dorta, R.; Dorta, R. Chiral dibenzazepine-
based P-alkene ligands and their rhodium complexes: catalytic
asymmetric 1,4 additions to enones. Organometallics 2008, 27,
[32]
[33]
Csók, Zs.; Keglevich, G.; Petꢀcz, G.; Kollár, L. Platinum
complexes of phospholes with reduced pyramidal character from
steric crowding. Inorg. Chem. 1999, 38, 831-833.
Keglevich, G.; Sipos, M.; Szieberth, D.; Petꢀcz, G.; Kollár, L. 4-
Chloro-5-methyl-3-diphenylphosphino-1-phenyl-1,2,3,6-tetrahy-
drophosphinine as a bidentate P-ligand in a cis chelate Pt(II)
complex. J. Organomet. Chem. 2004, 689, 3158-3162.
Keglevich, G.; Sipos, M.; Ujj, V.; Körtvélyesi, T. Synthesis of 3-
phosphinoxido- and 3-phosphono-1,2,3,4,5,6-hexahydrophos-
phinine oxides as potential precursors of bidentate P-ligands. Lett.
Org. Chem. 2005, 2, 608-612.
[
[
19]
20]
[34]
[35]
Kerényi, A.; Kovács, V.; Körtvélyesi, T.; Ludányi, K.; Drahos, L.;
6
605-6613.
Keglevich, G.
A
new family of platinum(II) complexes
[
[
21]
22]
Clark, T.P.; Landis, C.R. Recent developments in chiral
phospholane chemistry. Tetrahedron Asymmetry 2004, 15, 2123-
incorporating five- and six-membered cyclic phosphine ligands.
Heteroatom Chem. 2010, 21, (in press).
Keglevich, G.; Újszászy, K.; Szöllꢀsy, Á.; Ludányi, K.; Tꢀke, L.
Synthesis of phosphine-borane complexes of P-heterocycles. J.
Organomet. Chem. 1996, 516, 139-145.
König, T.; Habicher, W.D.; Hähner, U.; Pionteck, J.; Rüger, C.;
Schwetlick, K. Organophosphorus antioxidants. 12: synthesis and
NMR-spectroscopy of organophosphorus antioxidants and related-
compounds. J. Prakt. Chem. 1992, 334, 333-349.
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb,
M.A.; Cheeseman, J.R.; Montgomery, J.A. Jr.; Vreven, T.; Kudin,
K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone,
V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson,
G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.;
Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.;
Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross,
J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.;
Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.;
Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg,
J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.;
Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.;
Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.;
Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.;
Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.;
Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.;
Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A.;
Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh PA, 2003.
Harvey, J.N.; Heslop, K.M.; Orpen, A.G.; Pringle, P.G. Factors
2
127.
[36]
[37]
Jiang, Q.Z.; Jiang, Y.T.; Xiao, D.M.; Cao, P.; Zhang, X.M. Highly
enantioselective hydrogenation of simple ketones catalyzed by a
Rh-PennPhos complex. Angew. Chem. Int. Ed. Engl., 1998, 37,
1
100-1103.
[23]
[24]
[25]
Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M.
BIPNOR: A new, efficient bisphosphine having two chiral, non-
racemizable, bridgehead phosphorus centers for use in asymmetric
catalysis. Chem. Eur. J. 1997, 3, 1365-1369.
[38]
Scriban, C.; Glueck, D.S.; Golen, J.A.; Rheingold, A.L. Platinum-
catalyzed asymmetric alkylation of
Mechanism and origin of enantioselectivity. Organometallics 2007,
6, 1788-1800.
a secondary phosphine:
2
Anderson, B.J.; Glueck, D.S.; DiPasquale, A.G.; Rheingold, A.
Substrate and catalyst screening in platinum-catalyzed asymmetric
alkylation of bis(secondary) phosphines. Synthesis of an
enantiomerically
pure
C-2-symmetric
diphosphine.
Organometallics 2008, 27, 4992-5001.
[
[
26]
27]
Anderson, B.J.; Guino-o, M.A.; Glueck, D.S.; Golen, J.A.;
DiPasquale, A.G.; Liable-Sands, L.M.; Rheingold, A.L. Platinum-
catalyzed enantioselective tandem alkylation/arylation of primary
phosphines: asymmetric synthesis of P-stereogenic 1-
phosphaacenaphthenes. Org. Lett. 2008, 10, 4425-4428.
Keglevich, G.; Szelke, H.; Kerényi, A.; Kudar, V.; Hanusz, M.;
Simon, K.; Imre, T.; Ludányi, K. New chiral P-ligands: P-amino-
and P-cycloalkoxy dibenzo[c.e][1,2]oxaphosphorines. Tetrahedron
Asymmetry 2005, 16, 4015-4021.
[39]
2 2
controlling the relative stabilities of cis- and trans-[PtX L ]
[
28]
29]
Keglevich, G.; Kerényi, A.; Mayer, B.; Körtvélyesi, T.; Ludányi,
K. Platinum(II) complexes of 2-alkoxy-dibenzo[c.e][1,2]
oxaphosphorines. Trans. Metal Chem. 2008, 33, 505-510.
Keglevich, G. Synthesis and reactivity of 1-(2,4,6-
trialkylphenyl)phospholes having a flattened P-pyramid, in Targets
in Heterocyclic Systems; Attanasi, O.A.; Spinelli, D.; Eds. Italian
Society of Chemistry, 2002, Vol. 6, pp. 245-269.
Keglevich, G. 6-Membered P-heterocycles: 1,2-Dihydro-, 1,2,3,6-
tetrahydro- and 1,2,3,4,5,6-hexahydrophosphinine 1-oxides. Curr.
Org. Chem. 2006, 10, 93-111.
isomers: Chatt and Wilkins - 50 years on. Chem. Commun. 2003,
278-279.
[40]
[41]
Stewart, J.J.P. Optimization of parameters for semiempirical
methods V: modification of NDDO approximations and application
to 70 elements. J. Mol. Model. 2007, 13, 1173-1213.
Rezac, J.; Fanfrlik, J.; Salahub, D.; Hobza, P. Semiempirical
quantum chemical PM6 method augmented by dispersion and H-
bonding correction terms reliably describes various types of
noncovalent complexes. J. Chem. Theory Comp. 2009, 5, 1749-
1760.
[
[
30]
31]
[
Keglevich, G.; Szelke, H.; Kerényi, A.; Imre, T. Bis(dibenzo[c.e]
[42]
Schaftenaar, G.; Noordik, J.H. Molden: A pre- and post-processing
program for molecular and electronic structures. J. Comput-Aided
Mol. Des., 2000, 14, 123-134.
[
1,2]oxaphosphorino-)dichloroplatinum complexes. Trans. Metal
Chem. 2006, 31, 306-309.