Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninolThis publication is part of the web themed issue on fluorine chemistryElectronic supplementary information (ESI) available: Procedures, synthesis and characterization data of products 2-7, copies of 1H, 13C and19F NMR spectra of compounds 3, 4 and 7. See DOI: 10.1039/c0ob00424c

Two efficient routes are reported for the synthesis of both enantiomers of trifluoroalaninol in enantiopure form. The first pathway involves a Strecker-type reaction performed from a chiral trifluoromethyloxazolidine (Fox). The second route, which is more direct, involves, as a key step, the reduction of chiral oxazolidines or imines derived from ethyl trifluoropyruvate. Enantiopure ( R )- and ( S )-trifluoroalaninol were conveniently synthesized in a few steps from fluoral hemiacetal or ethyl trifluoropyruvate.