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Title: Asymmetric synthesis and the coordination chemistry of a P-chiral diphosphine monoxide
Authors: Teo, T.-W.
Selvaratnam, S.
Vittal, J.J. 
Leung, P.-H. 
Keywords: Asymmetric synthesis
Diels-Alder reaction
Diphosphine monoxide
Gold complexes
Palladium complexes
Issue Date: 6-Aug-2003
Citation: Teo, T.-W., Selvaratnam, S., Vittal, J.J., Leung, P.-H. (2003-08-06). Asymmetric synthesis and the coordination chemistry of a P-chiral diphosphine monoxide. Inorganica Chimica Acta 352 : 213-219. ScholarBank@NUS Repository.
Abstract: The organopalladium complex containing ortho-metalated (R)-(1-(dimethylamino)ethyl)-naphthalene as the chiral auxiliary has been used successfully to promote the asymmetric [4+2] exo-cycloaddition reaction between 1-phenyl-3,4-dimethylphosphole and vinyldiphenylphosphine oxide. The resulting P-chiral phosphanorbornene was obtained as a P-O bidenate chelate on the palladium template. The phosphanorbornene (-)-(L) could be liberated from the palladium template as a highly air-sensitive oil by the treatment of the template complex with aqueous potassium cyanide. Upon recoordination to the Au(I) ion, the diphosphine monoxide coordinated to Au(I) as a monodentate ligand via its tertiary phosphorus donor atom to form the linear complex (+)-[(L-P)AuCl]. The chloro ligand and the pendant P=O group in the gold complex showed significant hydrophilicity as they both formed hydrogen bondings to a water molecule. However, the neutral gold complex is not soluble in water. © 2003 Elsevier Science B.V. All rights reserved.
Source Title: Inorganica Chimica Acta
ISSN: 00201693
DOI: 10.1016/S0020-1693(03)00154-3
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