Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
Wuyuan Zhang (Chinese Academy of Sciences, TU Delft - BT/Biocatalysis)
Huanhuan Li (Xi’an Jiaotong University)
Sabry H.H. Younes (TU Delft - BT/Biocatalysis, Sohag University)
Patricia Gómez De Santos (Instituto de Catálisis y Petroleoquímica - CSIC)
Florian Tieves (TU Delft - BT/Biocatalysis)
Gideon Grogan (University of York)
Martin Pabst (TU Delft - BT/Environmental Biotechnology)
Miguel Alcalde (Instituto de Catálisis y Petroleoquímica - CSIC)
Adrian C. Whitwood (University of York)
Frank Hollmann (TU Delft - BT/Biocatalysis)
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Abstract
Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show that naphthalene epoxides generated by fungal peroxygenases can be subjected to nucleophilic ring opening, yielding non-racemic trans-disubstituted cyclohexadiene derivates, which in turn can be used for further chemical transformations. This approach may represent a promising shortcut for the synthesis of natural products and APIs.
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