Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones

✍ Scribed by Thomas F. Anderson; Julian G. Knight; Kirill Tchabanenko

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 162 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02677-1

✦ Synopsis

In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2ones gives stereoselectively the 3,6-anti diastereoisomer with MeI, BuI and i-PrI. Alkylation of the corresponding N-BOC pyridinones gives the 3,6-syn diastereoisomer with high selectivity.