Synfacts 2007(9): 0944-0944  
DOI: 10.1055/s-2007-968849
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Monofluoromethylation Using the Mitsunobu Reaction

Contributor(s): Mark Lautens, Michael Langer
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
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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.