Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

…, SA Haughey, MA Kennedy, JF Malone, SD Shepherd…

Index: Boyd, Derek R.; Sharma, Narain D.; Haughey, Simon A.; Kennedy, Martina A.; Malone, John F.; Shepherd, Steven D.; Allen, Christopher C. R.; Dalton, Howard Tetrahedron, 2004 , vol. 60, # 3 p. 549 - 559

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Citation Number: 29

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 ...