By the same authors

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Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene

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Author(s)

  • Gideon James Grogan
  • Adrian C. Whitwood
  • Wuyuan Zhang
  • Huanhuan Li
  • Sabry Younes
  • Patricia Gomez de Santos
  • Florian Tieves
  • Martin Pabst
  • Miguel Alcalde
  • Frank Hollmann

Department/unit(s)

Publication details

JournalACS Catalysis
DateAccepted/In press - 29 Jan 2021
DateE-pub ahead of print (current) - 12 Feb 2021
Volume11
Number of pages6
Pages (from-to)2644-2649
Early online date12/02/21
Original languageEnglish

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 transdisubstituted
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. Following the ring-opening reactions, the synthetic possibility of
cyclohexadiene derivates also demonstrated by four examples yielding functional compounds. This novel approach may
represent a promising shortcut for the synthesis of natural products and APIs.

Bibliographical note

© 2021 The Authors. Published by American Chemical Society

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