Grogan, Gideon James orcid.org/0000-0003-1383-7056, Whitwood, Adrian C., Zhang, Wuyuan et al. (7 more authors) (2021) Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene. ACS Catalysis. pp. 2644-2649. ISSN 2155-5435
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2021 The Authors. Published by American Chemical Society |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 17 Feb 2021 13:00 |
Last Modified: | 19 Mar 2025 00:09 |
Published Version: | https://doi.org/10.1021/acscatal.0c05588 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1021/acscatal.0c05588 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:171311 |