Stereoselective Monofluoromethylation Using the Mitsunobu Reaction
G. K. Prakash, S. Chacko, S. Alconcel, T. Stewart, T. Mathew, G. A. Olah*
Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, USA
23. August 2007 (online)
The synthesis of fluorine-containing compounds has attracted considerable interest recently due to the useful medicinal properties of organofluorine compounds. Whereas the direct nucleophilic asymmetric fluorination is still challenging, the authors present a method to introduce monofluoromethyl nucleophiles using the Mitsunobu reaction on a variety of aromatic and aliphatic alcohols. Due to the stereospecifity of this reaction, chiral alcohols react under Walden inversion mechanism to give the chiral fluoromethylated compounds. For some of the authors’ previous work on fluoroalkylation, see: Angew. Chem. Int. Ed. 2003, 42, 5216.