Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene

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

Research output: Contribution to journalArticlepeer-review


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.
Original languageEnglish
Pages (from-to)2644-2649
Number of pages6
JournalACS Catalysis
Early online date12 Feb 2021
Publication statusE-pub ahead of print - 12 Feb 2021

Bibliographical note

© 2021 The Authors. Published by American Chemical Society

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