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My research interests are primarily
concerned with the synthesis and resolution of tertiary arsines and
phosphines and, in particular, of asymmetric bidentate ligands
containing stereogenic arsenic and/or phosphorus donor atoms
My research interests are primarily
concerned with the synthesis and resolution of tertiary arsines and
phosphines and, in particular, of asymmetric bidentate ligands
containing stereogenic arsenic and/or phosphorus donor atoms. Such
ligands are not only potential chiral auxiliaries in asymmetric
synthesis and catalysis but furthermore, appropriately designed ligands
of this type are precursors to chiral quadridentate ligands containing
two or more stereogenic donor atoms. Several chiral quadridentate
ligands containing three 1,2-phenylene linkages have been synthesised
in a completely stereoselective manner using this approach. Optically
active ligands of this type also form a single diastereomer on
complexation to six coordinate transition metal ions and are seen as
potential chiral auxiliaries in asymmetric catalysis.
A second area of interest is in the
synthesis of chiral transition metal complexes as potential anticancer
drugs. A variety complexes of the type [MX2(bidentate)], [(MX2)(m-quadridentate)], [M'(bidentate)2]X
and [M'(quadridentate)]X [where M = Pt(II) or Pd(II); and M' = Au(I),
Ag(I) or Cu(I)] have been synthesised containing chiral ligands which
are derivatives of (2-aminoethyl)phosphine and
(2-aminophenyl)phosphine. Certain of these complexes exhibit
antiproliferative properties comparable to cisplatin. Furthermore, all
of the gold(I) complexes have been shown to rapidly accumulate in
mitochondria by virtue of their lipophilic, cationic nature and in most
cases to inhibit the activity of ATP synthase leading to rapid cell
death. Current work in this area is geared towards the development of
gold(I)-based antimitochondrial antitumour agents.
Selected Publications
- Completely Stereoselective Synthesis of a Chiral
Quadridentate with As2NP Donor Atoms. Crystal and Molecular Structure
of [OC-6-35-(R*,S*)]-(±)-Dichloro{1-[(2-dimethylarsino-
phenyl)methylarsino]-2-[(2-aminophenyl)methylphosphino]benzene-As,As’,N,P}cobalt(III)
Chloride Dihydrate. J. Chem. Soc., Chem. Commun., 1994,
1587 (with R. Doyle and A. C. Willis).
- Synthesis,Resolution and Reactions of
(±)-(2-Aminophenyl)methylphenylphosphine. Crystal and Molecular
Structure of
(R*,R*,S*,R*)-(±)-{1,3-Bis{[2-(methylphenyphosphino)
phenyl]amino}propane}nickel(II) Perchlorate. J. Chem. Soc., Dalton
Trans., 1995, 57 (with C. E. Barclay, G. Deeble, R. J.
Doyle, S. A. Elix, T. L. Jones, S. B. Wild and A. C. Willis).
- Stereoselective Synthesis of Chiral Multidentate
Ligands with As2NP or As4P Donor Atoms. J. Chem. Soc., Dalton Trans.,
1997, 2713 (with R. J. Doyle and A. C. Willis).
- Synthesis of Gold(I), Silver(I) and Copper(I)
Complexes Containing Substituted (2-Aminophenyl)phosphines. Molecular
Structures of [AuI(2-H2NC6H4PPh2)], [AuI{(±)-2-H2NC6H4PMePh)]
and (±)-[Cu(2-H2NC6H4PPh2)2]PF6. J. Chem. Soc., Dalton Trans.,
1997, 3435 (with R. J. Doyle and A. C. Willis).
- Antitumour Activity of Gold(I), Silver(I) and
Copper(I) Complexes Containing Chiral Tertiary Phosphines. Metal-Based
Drugs, 1998, 5, 217 (with M. J. McKeage, P.
Papathanasiou, A. Sjaarda, G. F. Swiegers, P. Waring and S. B. Wild).
- Completely Stereoselective Synthesis of a Chiral
Tetra(Tertiary Phosphine). Crystal and Molecular Structure of
[OC-6-22-(R*,R*)]-Dichloro{1,2-bis[(2-dimethylphosphinophenyl)-methylphosphino]benzene-P,P’,P’’,P’’’}cobalt(III)
hexafluorophophate. J. Chem. Soc., Dalton Trans., 2000,
1829 (with S. Chatterjee, R. J. Doyle, D. C. R. Hockless and A. C.
Willis).
- Synthesis of Chiral Multidentate Tertiary Arsines
with As4 or As6 Donor Atoms. J. Chem. Soc., Dalton Trans., 2000,
3603 (with R. J. Doyle, N. Habermehl and A. C. Willis).
Dr Geoff Salem is a PhD graduate of the
ANU (Research School of Chemistry) and is current Department Head.
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