Regioselective Control in the Reactions of α-Aminoalkylcuprates with Allylic Substrates

Academic Article

Abstract

  • Organocuprate reagents prepared from α-aminoalkyllithium reagents and CuCN react with allylic electrophiles to afford homoullylic amines. Allylic sulfides of benzothiazole-2-thiol give exclusively substitution products without rearrangement while cuprate reagents prepared from primary α-aminoalkyl ligands react with allylic bromides to give rearranged substitution products with modest regioselectivity. Chemical yields and regioselectivities are dependent upon solvent, substrate leaving group, added LiCl salt, and α-aminoalkyl ligand.
  • Digital Object Identifier (doi)

    Author List

  • Dieter RK; Velu SE; Nice LE
  • Start Page

  • 1114
  • End Page

  • 1116
  • Volume

  • 1997
  • Issue

  • 9