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

Research output: Contribution to journal › Article › Scientific › peer-review

169 Downloads (Pure)

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

Access to Document

10.1039/C6GC01926A

Enzymatic HalocyclizationFinal published version, 1.25 MBLicence: CC BY

1 Finished

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 → 31/03/2021
Project: Academy of Finland: Other research funding

Bioeconomy Research Infrastructure
Jukka Seppälä (Manager)
School of Chemical Engineering
Facility/equipment: Facility

Cite this

@article{cdaa2ecfabd44ec08b8a13f6ff5875c5,

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

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.",

author = "Janne Naapuri and Rolfes, {Julian D.} and Julia Keil and Sapu, {Chicco Manzuna} and Jan Deska",

year = "2017",

doi = "10.1039/C6GC01926A",

language = "English",

volume = "19",

pages = "447--452",

journal = "Green Chemistry",

issn = "1463-9262",

}

TY - JOUR

T1 - Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles

AU - Naapuri, Janne

AU - Rolfes, Julian D.

AU - Keil, Julia

AU - Sapu, Chicco Manzuna

AU - Deska, Jan

PY - 2017

Y1 - 2017

N2 - 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.

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.

U2 - 10.1039/C6GC01926A

DO - 10.1039/C6GC01926A

M3 - Article

VL - 19

SP - 447

EP - 452

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

ER -

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

Abstract

Access to Document

Fingerprint

Projects

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

Equipment

Bioeconomy Research Infrastructure

Cite this