Synthesis of benzylcyanoborane adducts of amines and separation of their enantiomers; SN2 substitution at boron atomExperimental procedures and characterization data for compounds 5, 6, 7, 8a–c as well as HPLC profiles are available as supplementary data. For direct electronic access see http://www.rsc.org/suppdata/cc/b0/b006265k/

Abstract

Benzylcyanoborane adducts of several amines were prepared in four steps from toluene, their enantiomers were separated using chiral phase HPLC and an S_N2 pathway was evidenced in the reaction of a trimethylamine-derived enantiomer with pyridine.