Enzymatic Bromocyclization of α- and γ-Allenols by Chloroperoxidase from Curvularia inaequalis

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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Date
2022-01-04
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en
Pages
6
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ChemistryOpen, Volume 11, issue 1
Abstract
Vanadate-dependent chloroperoxidase from Curvularia inaequalis catalyzes 5-endo-trig bromocyclizations of α-allenols to produce valuable halofunctionalized furans as versatile synthetic building blocks. In contrast to other haloperoxidases, also the more challenging 5-exo-trig halocyclizations of γ-allenols succeed with this system even though the scope still remains more narrow. Benefitting from the vanadate chloroperoxidase‘s high resiliency towards oxidative conditions, cyclization-inducing reactive hypohalite species are generated in situ from bromide salts and hydrogen peroxide. Crucial requirements for high conversions are aqueous biphasic emulsions as reaction media, stabilized by either cationic or non-ionic surfactants.
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| openaire: EC/H2020/865885/EU//ABIONYS Funding Information: We gratefully acknowledge financial support by the European Research Council (ABIONYS, 865885, J. D.), the Academy of Finland (grant numbers 298350 & 324976, J. D.), the NATO Science for Peace and Security Programme (EnzIL, G5713) and the Finnish Foundation for Technology Promotion (J. M. N.). Publisher Copyright: © 2022 The Authors. Published by Wiley-VCH GmbH
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Naapuri , J M , Wagner , P K , Hollmann , F & Deska , J 2022 , ' Enzymatic Bromocyclization of α- and γ-Allenols by Chloroperoxidase from Curvularia inaequalis ' , ChemistryOpen , vol. 11 , no. 1 , e202100236 . https://doi.org/10.1002/open.202100236