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

Journal article (2021)

Authors

W. Zhang Chinese Academy of Sciences, BT/Biocatalysis - AS
Huanhuan Li Xi’an Jiaotong University
S.H.H. Younes BT/Biocatalysis - AS , Sohag University
Patricia Gómez de Santos Institute of Catalysis, CSIC, Madrid
F. Tieves BT/Biocatalysis - AS
Gideon Grogan University of York
Martin Pabst BT/Environmental Biotechnology - AS
Miguel Alcalde Institute of Catalysis, CSIC, Madrid
Adrian C. Whitwood University of York
F. Hollmann BT/Biocatalysis - AS
Research Group
BT/Environmental Biotechnology (AS) (TU Delft)
Copyright: © 2021 W. Zhang, Huanhuan Li, S.H.H. Younes, Patricia Gómez De Santos, F. Tieves, Gideon Grogan, Martin Pabst, Miguel Alcalde, Adrian C. Whitwood, F. Hollmann
DOI: https://doi.org/10.1021/acscatal.0c05588
More Info
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Published Date

2021

Language

English

Faculty

Applied Sciences

Department

BT/Biotechnologie

Research Group

BT/Environmental Biotechnology

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.