Christophe Audouard

Enantioselective synthesis of BMS-204352 (MaxiPost™) using N-fluoroammonium salts of cinchona alkaloids (F–CA–BF4)

The enantioselective synthesis of a potent Maxi-K potassium channel opener (BMS-204352) mediated by N-fluoroammonium salts of cinchona alkaloids is described. Two synthetic pathways were evaluated. An ee as high as 88% was achieved (>99% after a single recrystallisation).

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

Abstract 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.

Enantioselective electrophilic fluorination in ionic liquids

It has been demonstrated that enantioselective electrophilic fluorination performed by means of N-fluorocinchonium salts in ionic liquids presents substantial advantages over the use of classical solvents.