Diastereocontrolled reduction of cyclic β-enaminones. A new diastereoselective route to 2,6-disubstituted piperidines

✍ Scribed by Stéphanie Fréville; Philippe Delbecq; Vu Moc Thuy; Huguette Petit; Jean Pierre Célérier; Gérard Lhommet

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 85 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00770-5

✦ Synopsis

A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (-)-pinidinone 1a, the (+)-dihydropinidine 1b and the (-)-pinidinol 1c were prepared from optically pure (6R)-6-methylpiperidin-2one 2. This method is based on the chemo-and diastereocontrolled reductions of an exocyclic b-enamino ketone.