Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions

Wuyuan Zhang, Huanhuan Li, Sabry H.H. Younes, Patricia Gómez De Santos, Florian Tieves, Gideon Grogan, Martin Pabst, Miguel Alcalde, Adrian C. Whitwood, Frank Hollmann

Research output: Contribution to journalArticleScientificpeer-review

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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.

Original languageEnglish
Pages (from-to)2644-2649
JournalACS Catalysis
Volume11
Issue number5
DOIs
Publication statusPublished - 2021

Keywords

  • arene epoxides
  • arene oxyfunctionalization
  • biocatalysis
  • chemoenzymatic reactions
  • naphthalene epoxides
  • oxidation
  • peroxygenase

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