Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

Derek R. Boyd*, Narain D. Sharma, John F. Malone, Vera Ljubez, Deirdre Murphy, Steven D. Shepherd, Christopher C R Allen

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Enantiopure β-hydroxy sulfoxides and catechol sulfoxides were obtained, by chemoenzymatic synthesis, involving dioxygenase-catalysed benzylic hydroxylation or arene cis-dihydroxylation and cis-diol dehydrogenase-catalysed dehydrogenation. Absolute configurations of chiral hydroxy sulfoxides were determined by X-ray crystallography, ECD spectroscopy and stereochemical correlation. The application of a new range of β-hydroxy sulfoxides as chiral ligands was examined.

Original languageEnglish
Pages (from-to)2651-2664
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number9
Early online date01 Feb 2016
DOIs
Publication statusPublished - 07 Mar 2016

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Sulfoxides
dehydrogenases
dehydrogenation
crystallography
ligands
synthesis
configurations
spectroscopy
x rays
Dioxygenases
Hydroxylation
X ray crystallography
X Ray Crystallography
Dehydrogenation
Spectrum Analysis
Spectroscopy
Ligands

Cite this

Boyd, Derek R. ; Sharma, Narain D. ; Malone, John F. ; Ljubez, Vera ; Murphy, Deirdre ; Shepherd, Steven D. ; Allen, Christopher C R. / Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 9. pp. 2651-2664.
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Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes. / Boyd, Derek R.; Sharma, Narain D.; Malone, John F.; Ljubez, Vera; Murphy, Deirdre; Shepherd, Steven D.; Allen, Christopher C R.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 9, 07.03.2016, p. 2651-2664.

Research output: Contribution to journalArticle

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AU - Malone, John F.

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AU - Murphy, Deirdre

AU - Shepherd, Steven D.

AU - Allen, Christopher C R

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