Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.
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.
Badioli
Michele
M
Department of Chemical Sciences, University of Camerino, Via S. Agostino 1, Italy.
Ballini
Roberto
R
Bartolacci
Massimo
M
Bosica
Giovanna
G
Torregiani
Elisabetta
E
Marcantoni
Enrico
E
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
D000577:Amides; D007659:Ketones; D009025:Morpholines; D009942:Organometallic Compounds; D010675:Pheromones; D002563:Cerium