Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes?

Organic & Biomolecular Chemistry Pub Date: 2016-02-01 DOI: 10.1039/C5OB02411K

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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