Synthesis and stereochemical study of new complexes of Pd and Pt with chiral dithioether ligands

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Abstract

New palladium(II) and platinum(II) complexes with two families of chiral dithioether ligands, (−)-1-benzyl-3,4-bis(methylsulfanyl)pyrrolidine (−)-degusMe2, (−)-1-benzyl-3,4-bis(isopropylsulfanyl)pyrrolidine (−)-degusPri2, (+)-1-benzyl-3,4-bis(phenylsulfanyl)pyrrolidine (+)-degusPh2, (−)-2,2-dimethyl-4,5-bis(methylsulfanylmethyl)-1,3-dioxolane (−)-diosMe2 and (−)-4,5-bis(isopropylsulfanylmethyl)-2,2-dimethyl-1,3-dioxolane (−)-diosPri2, have been prepared and characterised by NMR. The complexes [PdCl2{(−)-degusMe2}], [PdCl2{(+)-degusPh2}] and [PdCl2{(−)-diosMe2}] show a mixture of two diastereomers in solution at room temperature. VT-NMR indicates that there is no interconversion between diastereomers at room temperature. Complex [Pt(cod){(−)-diosMe2}][BF4]2 is extremely fluxional and its diastereomers did not show isolated NMR resonances even at −90 °C. The complexes [PdCl2{(−)-degusPri2}], [PdCl2{(−)-diosPri2}] and [Pt(cod){(−)-diosPri2}][BF4]2, which contain a more hindered ligand, seem to be well suited for use in enantioselective catalysis because only one diastereomer is present.

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