Abstract
A series of chiral non-racemic triorganotin halides and triorganotin hydrides containing one or two (1R,2S,5R)-menthyl (Men) substituents as well as 2-(4,4-dimethyl-2-oxazolinyl)-5-(methyl)phenyl (L) or chiral 2-(4-isopropyl-2-oxazolinyl)-5-(methyl)phenyl ligand (L*) have been synthesized and characterised. Each of SnCl(Men)PhL and SnH(Men)PhL has a stereogenic tin centre and were isolated in diastereomeric ratios of 70∶30 and 50∶50, respectively; SnCl(Men)PhL* and SnH(Men)PhL* were synthesized in diastereomeric ratios of 50∶50 and 66∶34, respectively. Single crystal X-ray analysis of SnCl(Men)2L and SnCl(Men)PhL reveals a tendency towards five co-ordination at the tin centre as a result of N→Sn interactions. AM1 calculations provide good qualitative predictability of the molecular geometries observed in the solid state as well as the diastereomeric ratios in solution.
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