Rearrangement of beta-amino alcohols and application to the synthesis of biologically active compounds.
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.
Cossy
Janine
J
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 75231-Paris Cedex 05, France. janine.cossy@espci.fr
Pardo
Domingo Gomez
DG
Dumas
Cécile
C
Mirguet
Olivier
O
Déchamps
Ingrid
I
Métro
Thomas-Xavier
TX
Burger
Benjamin
B
Roudeau
Rémi
R
Appenzeller
Jérôme
J
Cochi
Anne
A
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D004364:Pharmaceutical Preparations