First efficient preparation of enantiopure 10-bromofenchone: the key intermediate to C10-substituted fenchone-derived chiral sources

✍ Scribed by Antonio Garcı́a Martı́nez; Enrique Teso Vilar; Amelia Garcı́a Fraile; Santiago de la Moya Cerero; Beatriz Lora Maroto

• Book ID: 104231372
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 79 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01316-8

✦ Synopsis

The first efficient preparation of enantiopure 10-bromofenchone from commercially available fenchone is described. The synthetic procedure is based on two consecutive Wagner-Meerwein rearrangements of the fenchone skeleton, taking place straightforwardly in only three individual steps with a high overall yield. The ability of the bromine atom to be substituted by other functional groups makes 10-bromofenchone a key intermediate for the preparation of interesting C10-substituted fenchone-derived chiral sources, which are topologically different and analogous to well-known C10-substituted camphor-derived chiral tools.