Enantioresolution by the chiral phthalic acid method: absolute configurations of substituted benzylic alcohols.
Substituted benzylic alcohols were enantioresolved by the chiral phthalic acid method as follows; 1) esterification of racemic alcohols with chiral phthalic acid, 2) separation of a diastereomeric mixture of the esters formed by HPLC on silica gel, and 3) recovery of enantiopure alcohols from the separated esters. The absolute configurations of chiral phthalic acid esters of benzylic alcohols were unambiguously determined by the X-ray crystallography using the campharsultam moiety as the internal standard of absolute configuration.
Kosaka
M
M
Institute for Chemical Reaction Science, Tohoku University, Sendai, Japan.
Watanabe
M
M
Harada
N
N
D001592:Benzyl Alcohols / Q000737:chemistry*; D002621:Chemistry / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D010795:Phthalic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D001592:Benzyl Alcohols; D010795:Phthalic Acids; C032279:phthalic acid