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Enantioresolution by the chiral phthalic acid method: Absolute configurations of substituted benzylic alcohols
Author(s) -
Kosaka Masashi,
Watanabe Masataka,
Harada Nobuyuki
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<362::aid-chir11>3.0.co;2-t
Subject(s) - chemistry , enantiopure drug , phthalic acid , diastereomer , moiety , chirality (physics) , absolute configuration , organic chemistry , chiral column chromatography , chiral derivatizing agent , silica gel , high performance liquid chromatography , catalysis , enantioselective synthesis , chiral symmetry , physics , quantum mechanics , quark , nambu–jona lasinio model
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. Chirality 12:362–365, 2000. © 2000 Wiley‐Liss, Inc.