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.