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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.

Original publication

DOI

10.1021/acs.orglett.5b00880

Type

Journal article

Journal

Org Lett

Publication Date

01/05/2015

Volume

17

Pages

2254 - 2257

Keywords

Alanine, Boranes, Crystallography, X-Ray, Esters, Hydrocarbons, Fluorinated, Lithium Compounds, Molecular Structure, Stereoisomerism