Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles

Janne Naapuri; Julian D. Rolfes; Julia Keil; Chicco Manzuna Sapu; Jan Deska

doi:10.1039/C6GC01926A

Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles

Janne Naapuri, Julian D. Rolfes, Julia Keil, Chicco Manzuna Sapu, Jan Deska

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Abstract

Chloroperoxidase from Caldariomyces fumago catalyzes the aerobic oxidative halocyclization of allenic alcohols and carboxylates yielding functionalized furan and pyran heterocycles as valuable synthetic scaffolds. Thanks to an oxidase-initiated redox cascade, simple halide salts – in combination with air and glucose – act as stoichiometric reagents for the in situ generation of reactive halonium species. Under the mild reaction conditions in an aqueous emulsion medium, the stereochemical integrity of diastereoand enantioenriched allenes remains uncompromised and chiral dihydrofurans can be obtained via 5-endo-trig cyclizations with perfect axis-to-centre chirality transfer.

Original language	English
Pages (from-to)	447-452
Number of pages	6
Journal	Green Chemistry
Volume	19
DOIs	https://doi.org/10.1039/C6GC01926A
Publication status	Published - 2017
MoE publication type	A1 Journal article-refereed

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10.1039/C6GC01926A

Enzymatic HalocyclizationFinal published version, 1.25 MBLicence: CC BY

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Beyond Biosynthesis: Enzymes as Catalysts in Non-natural Synthetic Transformations

Blume, F., Jäger, C., Deska, J., Naapuri, J., Liu, Y. & Kiefer, A.

01/09/2016 → 31/08/2021

Project: Academy of Finland: Other research funding

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School of Chemical Engineering

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Cite this

Naapuri, J., Rolfes, J. D., Keil, J., Sapu, C. M., & Deska, J. (2017). Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles. Green Chemistry, 19, 447-452. https://doi.org/10.1039/C6GC01926A

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abstract = "Chloroperoxidase from Caldariomyces fumago catalyzes the aerobic oxidative halocyclization of allenic alcohols and carboxylates yielding functionalized furan and pyran heterocycles as valuable synthetic scaffolds. Thanks to an oxidase-initiated redox cascade, simple halide salts – in combination with air and glucose – act as stoichiometric reagents for the in situ generation of reactive halonium species. Under the mild reaction conditions in an aqueous emulsion medium, the stereochemical integrity of diastereoand enantioenriched allenes remains uncompromised and chiral dihydrofurans can be obtained via 5-endo-trig cyclizations with perfect axis-to-centre chirality transfer.",

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AU - Naapuri, Janne

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AU - Keil, Julia

AU - Sapu, Chicco Manzuna

AU - Deska, Jan

PY - 2017

Y1 - 2017

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AB - Chloroperoxidase from Caldariomyces fumago catalyzes the aerobic oxidative halocyclization of allenic alcohols and carboxylates yielding functionalized furan and pyran heterocycles as valuable synthetic scaffolds. Thanks to an oxidase-initiated redox cascade, simple halide salts – in combination with air and glucose – act as stoichiometric reagents for the in situ generation of reactive halonium species. Under the mild reaction conditions in an aqueous emulsion medium, the stereochemical integrity of diastereoand enantioenriched allenes remains uncompromised and chiral dihydrofurans can be obtained via 5-endo-trig cyclizations with perfect axis-to-centre chirality transfer.

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DO - 10.1039/C6GC01926A

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EP - 452

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JF - Green Chemistry

SN - 1463-9262

ER -