Formal [4+1] annulation of α,α-dialkyl β-oxo amides and dimethylsulfoxonium methylide: a synthetic route to β-hydroxy-γ-lactams

Chem Commun (Camb). 2013 Aug 25;49(66):7358-60. doi: 10.1039/c3cc43317j.

Abstract

A facile and efficient one-pot synthesis of β-hydroxy-γ-lactams from α,α-dialkyl β-oxo amides and trimethylsulfoxonium iodide in the presence of sodium hydride via a tandem Corey-Chaykovsky reaction and an intramolecular lactamization process is developed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Sodium Compounds / chemistry
  • Sulfonium Compounds / chemistry*
  • beta-Lactams / chemical synthesis*
  • beta-Lactams / chemistry

Substances

  • Amides
  • Sodium Compounds
  • Sulfonium Compounds
  • beta-Lactams
  • dimethylsulfoxonium methylide
  • sodium hydride