Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; S(N)2 substitution at boron atom

Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an S(N)2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.