81925-10-2Relevant academic research and scientific papers
Aminoalcohols II: Preparation of Enantiomerically Pure Pharmacologically Active β-Aminoalcohols
Noe, C. R.,Knollmueller, M.,Gaertner, P.,Fleischhacker, W.,Katikarides, E.
, p. 481 - 494 (2007/10/02)
A synthesis of β-aminoalcohols is described starting from racemic or enantiomerically pure α-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups.Reduction with lithium aluminium hydride yielded O-protected β-aminoalcohols.Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected aminoalcohols were separated.Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure β-aminoalcohols or their corresponding hydrochlorides. - Keywords: 1,2-Amino-alcohols, enantiomerically pure; Lithium aluminium hydride reduction
Chiral Lactols, II. Racemate Separation and Enantioselective Acetalisation with the 2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl Protective Group
Noe, Christian R.
, p. 1591 - 1606 (2007/10/02)
A simple method for the resolution of the chiral alcohols, cyanohydrins, thiols and amines rac-2a - f by the reaction with the chiral protective group 1a ( or 1b, respectively) is described.The diastereomeric derivatives 3a - f and 4a - f are separated by column chromatography or crystallisation.Subsequent methanolysis or hydrolysis, respectively, yields the enantiomers and the recovered protective group.With rac-2a - c preferential acetalisation of the (R)-enantiomers was observed.This phenomenon was investigated by modification of the protective group.Considerations on conformations of 3a point to an important role of the anomeric and exo-anomeric effect in this enantioselective reaction.
