title: Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.
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.
authors.affiliation: Department of Chemical Sciences, University of Camerino, Via S. Agostino 1, Italy.
authors.forename: Michele
authors.initials: M
authors.lastname: Badioli
authors.forename: Roberto
authors.initials: R
authors.lastname: Ballini
authors.forename: Massimo
authors.initials: M
authors.lastname: Bartolacci
authors.forename: Giovanna
authors.initials: G
authors.lastname: Bosica
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Torregiani
authors.forename: Enrico
authors.initials: E
authors.lastname: Marcantoni
mesh_terms: D000577:Amides / Q000737:chemistry; D000818:Animals; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis; D007915:Lepidoptera / Q000502:physiology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D007659:Ketones; D009025:Morpholines; D009942:Organometallic Compounds; D010675:Pheromones; D002563:Cerium