New chiral tin compounds containing the 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand

A series of tri- and tetraorganotin compounds containing the optically active 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand and tert-butyl, methyl and/or phenyl groups on the tin has been synthesized. All the novel compounds have been characterized, especially by means of the multinuclear NMR investigation, the results of which are discussed. The tin halides, as pairs of diastereoisomers in solution, crystallize in the form of one diastereoisomer. The single-crystal X-ray analysis of tin iodide 10a revealed pseudo-equatorial position of the tert-butyl group opposite to the isopropyl group. In the corresponding diastereomeric tin hydrides values of 1J(1H–117/119Sn) differ significantly, suggesting a different pseudo-axial/equatorial position of the hydrogen atom.

Graphical abstractA series of tri- and tetraorganotin compounds containing the optically active 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand and tert-butyl, methyl and/or phenyl groups on the tin has been synthesized. The tin halides, as pairs of diastereoisomers in solution, crystallize in the form of one diastereoisomer. In the corresponding diastereomeric tin hydride values of the 1J(1H–117/119Sn) differ significantly, suggesting a different pseudo-axial/equatorial position of the hydrogen atom.Figure optionsDownload full-size imageDownload as PowerPoint slide