An enantioselective synthesis of isoquinuclidines from 3-substituted chiral pyridinium salts

✍ Scribed by Daniela Cristina dos Santos; Rossimiriam P de Freitas Gil; Laurent Gil; Christian Marazano

• Book ID: 104231251
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 63 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01194-7

✦ Synopsis

A new enantioselective approach to chiral isoquinuclidines, such as 15, 18 and 21, is reported. The key step of these syntheses is a cycloaddition between chiral dihydropyridines 14 or 20, now readily available from tetrahydropyridinium salts 6 or 11, and achiral dienophiles. The reaction proceeds with a very good endo-selectivity and moderate d.e.