The cyclometalation of chiral secondary amines through
ortho-metalation of an aryl group occurredreadily with [(
6-benzene)RuCl
2]
2 in acetonitrile. Reasonable to good yields of the expected cationicproducts of the form [(
6-benzene)Ru(N-C)(NCMe)](PF
6), in which N-C represents the cyclometalatedligands, were obtained with bis-(
R)-phenylethylamine, bis-(
R)-1-naphthylethylamine, and (2
R,5
R)-2,5-diphenylpyrrolidine. Variable proportions of the expected four diastereoisomers were found according toNMR studies. The stereochemistry of complexes was investigated by 2D NMR in solution and by X-raydiffraction of single crystals. The (
S) configuration at the metal was generally associated with a
![](/images/gifchars/delta.gif)
conformation of the metallacycle, and conversely, the (
R) configuration with the
![](/images/gifchars/lambda.gif)
conformation.