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Enantiopurity and absolute configuration determination of arene cis ‐dihydrodiol metabolites and derivatives using chiral boronic acids
Author(s) -
Boyd Derek R.,
Sharma Narain D.,
Goodrich Peter A.,
Malone John F.,
McConville Gareth,
Harrison John S.,
Stevenson Paul J.,
Allen Christopher C.R.
Publication year - 2018
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/chir.22764
Subject(s) - enantiopure drug , chemistry , phenylboronic acid , diol , boronic acid , absolute configuration , alkene , enantiomer , stereochemistry , chiral column chromatography , chiral derivatizing agent , organic chemistry , enantioselective synthesis , catalysis
The relative merits of the methods employed to determine enantiomeric excess ( ee ) values and absolute configurations of chiral arene and alkene cis ‐1,2‐diol metabolites, including boronate formation, using racemic or enantiopure (+) and (−)‐2‐(1‐methoxyethyl)phenylboronic acid (MEPBA), are discussed. Further applications of: 1) MEPBA derived boronates of chiral mono‐ and poly‐cyclic arene cis ‐dihydrodiol, cyclohex‐2‐en‐1‐one cis ‐diol, heteroarene cis / trans ‐2,3‐diol, and catechol metabolites in estimating their ee values, and 2) new chiral phenylboronic acids, 2‐[1‐methoxy‐2,2‐dimethylpropyl]phenyl boronic acid (MDPBA) and 2‐[1‐methoxy‐1‐phenylmethyl]phenyl boronic acid (MPPBA) and their advantages over MEPBA, as reagents for stereochemical analysis of arene and alkene cis ‐diol metabolites, are presented.