Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids

Derek R Boyd, Narain D. Sharma, Peter A Goodrich, John F Malone, Gareth McConville, John S Harrison, Paul J Stevenson, Christopher C R Allen

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1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5-18
JournalChirality
Volume30
Issue number1
Early online date11 Oct 2017
DOIs
Publication statusPublished - Jan 2018

Keywords

  • Journal Article

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