Dynamic Kinetic Resolution and Desymmetrization Processes: A Straightforward Methodology for the Enantioselective Synthesis of Piperidines

✍ Scribed by Mercedes Amat; Oriol Bassas; Núria Llor; Margalida Cantó; Maria Pérez; Elies Molins; Joan Bosch

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 207 KB
• Volume: 12
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200600420

✦ Synopsis

Abstract

A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non‐racemic oxazolo[3,2‐a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)‐phenylglycinol or other amino alcohols with racemic or prochiral δ‐oxo (di)acid derivatives in highly stereoselective processes involving dynamic kinetic resolution and/or desymmetrization of diastereotopic or enantiotopic ester groups.