Journal
CHEMISTRYOPEN
Volume 11, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/open.202100236
Keywords
allenes; cyclization; halogenation; haloperoxidase; heterocycles
Categories
Funding
- European Research Council (ABIONYS) [865885]
- Academy of Finland [298350, 324976]
- NATO Science for Peace and Security Programme (EnzIL) [G5713]
- Finnish Foundation for Technology Promotion
- European Research Council (ERC) [865885] Funding Source: European Research Council (ERC)
- Academy of Finland (AKA) [324976] Funding Source: Academy of Finland (AKA)
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Vanadate-dependent chloroperoxidase can catalyze halogenation reactions of alpha-allenols and gamma-allenols to produce valuable halofunctionalized furans. Reactive hypohalite species are generated in situ from bromide salts and hydrogen peroxide, and the reaction system is stabilized by aqueous biphasic emulsions.
Vanadate-dependent chloroperoxidase from Curvularia inaequalis catalyzes 5-endo-trig bromocyclizations of alpha-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 gamma-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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