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Updated: Apr 15, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Asymmetric Synthesis of Substituted anti-β-Fluorophenylalanines
Stephen G Davies1, Ai M Fletcher1, Aileen B Frost1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
Abstract:
A range of substituted anti-β-fluorophenylalanines was produced from the corresponding enantiopure α-hydroxy-β-amino esters using a stereospecific XtalFluor-E promoted rearrangement procedure as the key step. The requisite substrates are readily produced via aminohydroxylation of an α,β-unsaturated ester using our lithium amide conjugate addition methodology and, following rearrangement, deprotection of the resultant enantiopure β-fluoro-α-amino esters gives the corresponding enantiopure anti-β-fluorophenylalanines in good yield and high diastereoisomeric purity.
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