N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agent

✍ Scribed by Dominique Cahard; Christophe Audouard; Jean-Christophe Plaquevent; Loic Toupet; Nicolas Roques

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 92 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00017-x

✦ Synopsis

The first ever enantiopure N-fluoro quaternary ammonium salt of cinchonidine (F-CD-BF 4 ) was prepared as an enantioselective fluorinating agent. A one-step transfer-fluorination of the quinuclidine moiety with Selectfluor ® gave the [N F] + reagent. The X-ray structure of F-CD-BF 4 was determined, which shows the N F distance (1.409(7) A , ) close to that found in other N F compounds.