Over the past decade, fluorine chemistry has seen increased interest in the pharmaceutical and agrochemical industries. Due to the recent demand of fluorinated organic molecules and limited means for their preparation, new methodologies are needed. This research focuses on developing a new methodology for the stereoselective nucleophilic addition of trimethylsilyl cyanide (TMSCN) to a-fluorocarbonyls (ketones and imines) mediated by Lewis base catalysts. It has been shown that the reaction time can be vastly reduced with the addition of various Lewis bases. This new method is efficient and produces the desired products in high yields (98%) and diastereoselectivity (9:1 cis:trans). These products can serve as direct precursors for a variety of biologically relevant molecules including unnatural fluorinated amino acids.

Developing new methodologies for the Lewis base catalyzed addition to a-fluorocarbonyls

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.