Diastereoselective conjugate addition of organocuprates to 3,4-dimethyl-5,6-dihydro-2(1H)-pyridinones. A concise synthesis of trans-3,4-dimethyl-4-phenylpiperidines.
[reaction: see text] Conjugate addition of aryl or alkyl cuprates to 3,4-dimethyl-5,6-dihydro-2(1H)-pyridinones led to diastereoisomerically pure 3,4,4-trisubstituted 2-piperidinones in 39-78% yields. The yields and the diastereochemistry of piperidinones depended on both the N-protecting group and the organocuprate. Reduction then deprotection of the trans-3,4-dimethyl-4-phenyl product provided the corresponding piperidine, analogue of a key precursor of opioid receptor antagonists.
Oueslati
Farhana
F
Groupe de Développements Méthodologiques en Tomographie par Emission de Positons, UMR CEA 2E, Université de Caen-Basse Normandie, Centre Cyceron, 15 Boulevard Henri Becquerel, BP 5229, F-14074 Caen Cedex, France.
Perrio
Cécile
C
Dupas
Georges
G
Barré
Louisa
L
D006859:Hydrogen / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009292:Narcotic Antagonists; D010880:Piperidines / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D009292:Narcotic Antagonists; D010880:Piperidines; D011728:Pyridones; D006859:Hydrogen