Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions.
Dehydropiperidinones stereoselectively obtained from N-arabinosyl imines were iodinated at the enaminone structure. Knochel iodine-magnesium exchange afforded Grignard compounds of these piperidinone derivatives which reacted, either directly or after transmetalation to zinc or copper intermediates, with alkyl-, aryl- or acylhalides to give correspondingly substituted piperidinones. Stereoselective conjugate allyl cuprate addition to a thus obtained 5-allyl dehydropiperidinone and ring-closing metathesis of the product gave a hydroquinolinone containing three stereogenic centers.
Kranke
Birgit
B
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Kunz
Horst
H
D002625:Chemistry, Organic / Q000379:methods*; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010881:Piperidones / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D007097:Imines; D009942:Organometallic Compounds; D010881:Piperidones; D003300:Copper; D007455:Iodine; D008274:Magnesium; D015032:Zinc