ChemInform Abstract: Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines.

✍ Scribed by Daniele Simoni; Marinella Roberti; Riccardo Rondanin; Alan P. Kozikowski

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199933244

✦ Synopsis

Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines.

-Asymmetric deprotonation of the racemic ketone (I) using chiral lithium amides provides ready access to the non-racemic β-ketoesters (III), which can be easily transformed into 8-oxa-norcocaine (VII) and 8-oxapseudonorcocaine (VIII) via reduction [→ (IV), (V)] followed by benzolylation. -(SIMONI, DANIELE;