title: Rearrangement of beta-amino alcohols and application to the synthesis of biologically active compounds.
abstract: Beta-amino alcohols derived from natural amino acids have been used extensively as a powerful source of chirality. Transformation of the hydroxy group of these beta-amino alcohols into a good leaving group, by using trifluoroacetic anhydride, led to rearranged beta-amino alcohols in good yields and with high enantiomeric excesses. This rearrangement has allowed the transformation of substituted prolinols to substituted 3-hydroxypiperidines and linear beta-amino alcohols, issued from natural amino acids, to rearranged beta-amino alcohols.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 75231-Paris Cedex 05, France. janine.cossy@espci.fr
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Domingo Gomez
authors.initials: DG
authors.lastname: Pardo
authors.forename: Cécile
authors.initials: C
authors.lastname: Dumas
authors.forename: Olivier
authors.initials: O
authors.lastname: Mirguet
authors.forename: Ingrid
authors.initials: I
authors.lastname: Déchamps
authors.forename: Thomas-Xavier
authors.initials: TX
authors.lastname: Métro
authors.forename: Benjamin
authors.initials: B
authors.lastname: Burger
authors.forename: Rémi
authors.initials: R
authors.lastname: Roudeau
authors.forename: Jérôme
authors.initials: J
authors.lastname: Appenzeller
authors.forename: Anne
authors.initials: A
authors.lastname: Cochi
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D004364:Pharmaceutical Preparations