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Elsevier, Journal of Organometallic Chemistry, (637-639), p. 116-125

DOI: 10.1016/s0022-328x(01)00880-4

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Chiral ferrocenylthiazolidines, new ligands for palladium complexes

Journal article published in 2001 by Asensio González, Jaume R. Granell ORCID, Concepción López
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The reaction of ferrocene with methyl or ethyl esters of l-cysteine in the presence of paraformaldehyde is studied. This process yields the optically pure derivatives: methyl or ethyl (R)-3-(ferrocenylmethyl)thiazolidine-4-carboxylates (1a or 1b), together with the corresponding N,N-bisthiazolidine derivatives (2a or 2b). When the reaction was carried out using the ethyl ester of l-cysteine, small amounts (ca. 9%) of the 1,1’-disubstituted ferrocene derivative (3b) were also isolated. The reactivity of compounds 1 versus palladium(II) species is studied, and has allowed us to isolate and characterise: [Pd(η3-C3H5)Br(1a)] (4a) and [Pd(η3-C3H5)Br(1b)] (4b), in which the ferrocenyl ligand behaves as a monodentate S-donor group. Compounds 4 evolve in the presence of dimethylsulfoxide to produce: [Pd(η1-C3H5)Br(1)(dmso)] (5) in which the palladium(II) is bound to the terminal carbon of the C3H5 group. The reactivity of ligands 1 with Na2[PdCl4] is also reported and has allowed us to isolate the dinuclear compounds [Pd2Cl4(μ-1a)2] (6a) and [Pd2Cl4(μ-1b)2] (6b)] in which the thiazolidine behaves as a bridging (N,S) donor group.