A new enzymatic enantioselective synthesis of dialkyl sulfoxides catalysed by monooxygenases

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Stefano Colonna, Nicoletta Gaggero, Giacomo Carrea and Piero Pasta


Abstract

Numerous dialkyl sulfides were enantioselectively oxidized to optically active sulfoxides catalysed by chloroperoxidase or cyclohexanone monooxygenase.


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