Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata

J Org Chem. 2002 Dec 13;67(25):8938-42. doi: 10.1021/jo0263061.

Abstract

Readily preparable morpholine amides hitch in good yields with organocerium reagents to produce ketones. Even in the presence of substrates and reagents with high steric hindrance, the organometallic compounds prepared from dry cerium(III) chloride and organomagnesium or organolithium compounds at -78 degrees C add cleanly to morpholine amides. The low cost of starting materials makes this new scheme of synthesis very interesting for the preparation of biologically important pheromones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Animals
  • Catalysis
  • Cerium / chemistry*
  • Ketones / chemical synthesis
  • Lepidoptera / physiology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Morpholines / chemistry*
  • Organometallic Compounds / chemistry*
  • Pheromones / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Amides
  • Ketones
  • Morpholines
  • Organometallic Compounds
  • Pheromones
  • Cerium