Unprecedented Formation of a Benzo[d]azepine by Acid-Catalyzed Cyclization of a Camphor-Derived N-Formylenamine

✍ Scribed by Gerrit J. Meuzelaar; Anders Blom; Leendert Maat; Roger A. Sheldon

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 112 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199902)1999:2<519::aid-ejoc519>3.0.co;2-r

✦ Synopsis

A convenient synthesis of (-)-N-styryl-N- [2-(1,7,7-trimethyl-yl)ethanol (6). Cyclization of the N-formylenamine 2 with the aid of 9-borabicyclo[3.3.1]non-9-yl triflate yielded a methano-bicyclo[2.2.1]hept-2-enyl)ethyl]formamide (2) was developed starting from natural (+)-camphor (3) via (-)-2-(bornen-2-bridged octahydro-1H-benzo[d]azepine derivative.