title: Asymmetric Synthesis of Substituted anti-β-Fluorophenylalanines.
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.
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
authors: Stephen G
authors: SG
authors: Davies
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
authors: Ai M
authors: AM
authors: Fletcher
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
authors: Aileen B
authors: AB
authors: Frost
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
authors: Paul M
authors: PM
authors: Roberts
authors: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
authors: James E
authors: JE
authors: Thomson
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004952:Esters; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001880:Boranes; D004952:Esters; D006845:Hydrocarbons, Fluorinated; D018020:Lithium Compounds; C571211:lithium amidoborane; D000409:Alanine