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

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‐...

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Detalles Bibliográficos
Autores principales: Naapuri, Janne M., Wagner, Philip K., Hollmann, Frank, Deska, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8734111/
https://www.ncbi.nlm.nih.gov/pubmed/34981903
http://dx.doi.org/10.1002/open.202100236
Descripción
Sumario: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.