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

作者：Oueslati Farhana^*; Perrio Cecile; Dupas Georges; Barre Louisa

来源：Organic Letters, 2007, 9(1): 153-156.

DOI：10.1021/ol062708+

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.

• 出版日期2007-1-4
• 单位中国地震局