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Abstract
A series of chiral non-racemic triorganotin halides and triorganotin hydrides containing one or two (1 R,2 S,5 R)-menthyl (Men) substituents as well as the 8-dimethylaminonaphthyl (L) or 2-[(1 S)-1-dimethylaminoethyl]phenyl (L*) substituents has been synthesised and characterised. Each of the compounds MenPhLSnBr ( 1) and MenPhLSnH ( 2) has a stereogenic tin centre and the compounds were isolated in diastereomeric ratios of 60:40 and 66:33, respectively. Compounds MenPhL*SnCl ( 3) and MenPhL*SnH ( 4) were synthesised with diastereomeric ratios of 73:27 and 64:36, respectively. Single crystal X-ray analysis of MenPhL*SnCl ( 3), Men 2L*SnCl ( 8), and MenPh 2LSn ( 10) reveals that each structure has a tendency towards penta-coordination at the tin centre as a result of intramolecular N→Sn interactions. AM1 calculations successfully predict the molecular geometries observed in the solid state as well as the diastereomeric ratios observed in solution.
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