Lewis acid complexed azacarbanions: Novel reactive intermediates of wide synthetic utility

Abstract

The concept of facilitating α-deprotonation of tertiary amines by complexation with Lewis acids is described. Treatment of BF3- amine complexes with strong bases resulted in deprotonation at benzylic, allylic, vinylic, α-pyridyl and unactivated primary or secondary carbons. Reaction with electrophiles afforded easy access to compounds with isoquinoline, morphinane and quinuclidine frameworks.