Journal | ACS Catalysis |
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Date | Accepted/In press - 29 Jan 2021 |
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Date | E-pub ahead of print (current) - 12 Feb 2021 |
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Volume | 11 |
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Number of pages | 6 |
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Pages (from-to) | 2644-2649 |
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Early online date | 12/02/21 |
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Original language | English |
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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.
© 2021 The Authors. Published by American Chemical Society