4.5 Article

Enzymatic Synthesis of Novel Chiral Sulfoxides Employing Baeyer-Villiger Monooxygenases

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 33, Pages 6409-6416

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000890

Keywords

Biocatalysis; Monooxygenases; Oxidation; Sulfur; Enantioselectivity

Funding

  1. Spanish Ministerio de Ciencia e Innovacion (MICINN)
  2. European Social Fund
  3. Ministerio de Educacion y Ciencia (MEC) [CTQ 2007-61126]
  4. EU

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Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising bio-transformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions.

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