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Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides
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UNSPECIFIED. (2004) Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides. TETRAHEDRON, 60 (3). pp. 549-559. ISSN 0040-4020
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Official URL: http://dx.doi.org/10.1016/j.tet.2003.10.107
Abstract
Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfoxide diastereoisomers, formed from the reaction of the (R)-1,3-benzodithiole-1-oxide metabolite with n-butyllithium and benzaldehyde, were separated and stereochemically assigned. Treatment, of enantiopure (1R,3R)-benzo-1,3-dithiole-1,3-dioxide, obtained by chemoenzymatic synthesis, with alkyllithium reagents, resulted in a novel ring-opening reaction which proceeded with inversion of configuration to yield a series of acyclic disulfoxides. (C) 2003 Elsevier Ltd. All rights reserved.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | TETRAHEDRON |
| Publisher: | PERGAMON-ELSEVIER SCIENCE LTD |
| ISSN: | 0040-4020 |
| Date: | 12 January 2004 |
| Volume: | 60 |
| Number: | 3 |
| Number of Pages: | 11 |
| Page Range: | pp. 549-559 |
| Identification Number: | 10.1016/j.tet.2003.10.107 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/8860 |
Data sourced from Thomson Reuters' Web of Knowledge
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