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 |
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Authors: | Oueslati Farhana Perrio Cécile Dupas Georges Barré Louisa |
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Institution: | 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. |
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Abstract: | 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. |
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