The exo-selectivity of the new non-natural chiral auxiliary (+)-(1R,endo)-2-benzonorbornenol in an asymmetric aza-Diels–Alder reaction

✍ Scribed by Franco Fernández; Xerardo Garcı́a-Mera; José Enrique Rodrı́guez-Borges; Marı́a Luisa C. Vale

• Book ID: 104252700
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 95 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02599-6

✦ Synopsis

The recently reported compound (+)-(1R,endo)-2-benzonorbornenol (2) proved to be an efficient chiral auxiliary in the asymmetric aza-Diels-Alder reaction between cyclopentadiene and the N-benzyl imine of its glyoxylate, which afforded a virtually all-exo mixture of cycloaducts with a 1S:1R diastereomeric ratio of 63:37.