Issue 9, 2016
From the journal:

Organic & Biomolecular Chemistry

Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes†

Derek R. Boyd,*a   Narain D. Sharma,a   John F. Malone,a   Vera Ljubez,a   Deirdre Murphy,a   Steven D. Shepherda  and  Christopher C. R. Allenb  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Queen's University, Belfast BT9 5AG, UK
E-mail: dr.boyd@qub.ac.uk
Fax: +44 (0)-28-9097-4687

b School of Biological Sciences, Queen's University of Belfast, Belfast, UK

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.

Graphical abstract: Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

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Article information

DOI
https://doi.org/10.1039/C5OB02411K
Article type
Paper
Submitted
23 Nov 2015
Accepted
22 Jan 2016
First published
01 Feb 2016

Org. Biomol. Chem., 2016,14, 2651-2664

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Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes

D. R. Boyd, N. D. Sharma, J. F. Malone, V. Ljubez, D. Murphy, S. D. Shepherd and C. C. R. Allen, Org. Biomol. Chem., 2016, 14, 2651 DOI: 10.1039/C5OB02411K

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