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

Research output: Contribution to journalArticle

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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

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Boronic Acids
Metabolites
Derivatives
Acids
Alkenes
Olefins
benzeneboronic acid
trans-1,2-dihydro-1,2-naphthalenediol

Keywords

  • Journal Article

Cite this

Boyd, Derek R ; Sharma, Narain D. ; Goodrich, Peter A ; Malone, John F ; McConville, Gareth ; Harrison, John S ; Stevenson, Paul J ; Allen, Christopher C R. / Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids. In: Chirality. 2018 ; Vol. 30, No. 1. pp. 5-18.
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Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids. / Boyd, Derek R; Sharma, Narain D.; Goodrich, Peter A; Malone, John F; McConville, Gareth; Harrison, John S; Stevenson, Paul J; Allen, Christopher C R.

In: Chirality, Vol. 30, No. 1, 01.2018, p. 5-18.

Research output: Contribution to journalArticle

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AU - Boyd, Derek R

AU - Sharma, Narain D.

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AU - Harrison, John S

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AU - Allen, Christopher C R

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