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

doi:10.1039/c5ob02411k

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 journal › Article › peer-review

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 language	English
Pages (from-to)	2651-2664
Number of pages	14
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	9
Early online date	01 Feb 2016
DOIs	https://doi.org/10.1039/c5ob02411k
Publication status	Published - 07 Mar 2016

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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title = "Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes",

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.",

author = "Boyd, {Derek R.} and Sharma, {Narain D.} and Malone, {John F.} and Vera Ljubez and Deirdre Murphy and Shepherd, {Steven D.} and Allen, {Christopher C R}",

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T1 - Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

AU - Boyd, Derek R.

AU - Sharma, Narain D.

AU - Malone, John F.

AU - Ljubez, Vera

AU - Murphy, Deirdre

AU - Shepherd, Steven D.

AU - Allen, Christopher C R

PY - 2016/3/7

Y1 - 2016/3/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84959227427&partnerID=8YFLogxK

U2 - 10.1039/c5ob02411k

DO - 10.1039/c5ob02411k

M3 - Article

AN - SCOPUS:84959227427

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VL - 14

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EP - 2664

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

Abstract

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