Chemoenzymatic synthesis of enantiopure hydroxy sulfoxides derived from substituted arenes. Issue 9 (1st February 2016)

• Record Type: Journal Article
• Authors: Boyd, Derek R.; Sharma, Narain D.; Malone, John F.; Ljubez, Vera; Murphy, Deirdre; Shepherd, Steven D.; Allen, Christopher C. R.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 9(2016)
• Page Start: 2651
• Page End: 2664
• Publication Date: 2016-02-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02411k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Enantiopure β-hydroxy sulfoxides, phenol sulfoxides and catechol sulfoxides were obtained by chemoenzymatic synthesis and evaluated as chiral synthons and ligands. 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.