3+2 Cycloadditions on azomethine ylides

CHED 505

Jeffrey P Backous, backouje@mnstate.edu and Craig P. Jasperse, jasperse@mnstate.edu. Department of Chemistry, Minnesota State University Moorhead, 1104 7th Ave S, Moorhead, MN 56563
  3+2 cycloadditions on the azomethine ylide derived from substrate 2 to give products 3 have been explored.  The substrate 2 was synthesized from 1-tetralone 1 via a 3-step protocol.  The Schmidt reaction converts 1-tetralone (1) to an amide. Amide reduction with LiAlH4 generates amine, followed by amine alkylation forming 2.  NBS oxidation of 2 generates an iminium ion, which upon treatment with base generates an azomethine ylide dipole.  Cycloadditions with achiral or chiral enoyl oxazolidinones (4) were explored using unsaturated alkene 4 and analogs.