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Dynamic Asymmetric Hemithioacetal Transformation by Lipase-Catalyzed γ-Lactonization: In Situ Tandem Formation of 1,3-Oxathiolan-5-one Derivatives

Authors

  • Dr. Morakot Sakulsombat,

    1. KTH Royal Institute of Technology, Department of Chemistry, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791233
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  • Yan Zhang,

    1. KTH Royal Institute of Technology, Department of Chemistry, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791233
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  • Prof. Olof Ramström

    Corresponding author
    1. KTH Royal Institute of Technology, Department of Chemistry, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791233
    • KTH Royal Institute of Technology, Department of Chemistry, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791233
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Abstract

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Dynamic hemithioacetal systems were efficiently generated in organic solvents and subsequently allowed to react with a range of lipases. This resulted in direct, dynamic asymmetric transformation of the systems, leading to optically active 1,3-oxathiolan-5-one products. The tandem process identified lipase-catalyzed lactonization as a useful method for the resolution of optimal constituents with high chemo- and stereoselectivities.

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