New Synthetic Pathways to Nitrogen Heterocycles

✍ Scribed by Laschat, Sabine

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 945 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970104

✦ Synopsis

Abstract

Novel Lewis acid‐catalyzed cyclizations of N‐arylimines and N‐benzylimines derived from amino acids and terpenes allow the diastereoselective preparation of octahydroacridines, indolizino[3,4‐b]quinolines, indolizidines, quinolizidines and piperidines. Although these two types of reactions can be classified as formal hetero‐Diels‐Alder and hetero‐ene reactions respectively, both proceed stepwise via cationic intermediates, which allow stereochemical control via chelate complexes. Stereochemical and mechanistical studies are described briefly.