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

Kemian ja materiaalitieteen laitos

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

35 Viittaukset (Web of Science)

294 Lataukset (Pure)

Abstrakti

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.

Alkuperäiskieli	Englanti
Sivut	447-452
Sivumäärä	6
Julkaisu	Green Chemistry
Vuosikerta	19
DOI - pysyväislinkit	https://doi.org/10.1039/C6GC01926A
Tila	Julkaistu - 2017
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Pääsy asiakirjaan

10.1039/C6GC01926A

Enzymatic HalocyclizationFinal published version, 1,25 MBLisenssi: CC BY

1 Päättynyt

Enzymer som katalysatorer i icke-naturliga syntetiska transformationer
Deska, J. (Vastuullinen johtaja), Jäger, C. (Projektin jäsen), Rothemann, A. (Projektin jäsen), Naapuri, J. (Projektin jäsen), Haase, M. (Projektin jäsen), Blume, F. (Projektin jäsen), Carmona Pichardo, M. (Projektin jäsen), Gregori, B. (Projektin jäsen), Liu, Y.-C. (Projektin jäsen), Schatton, M. (Projektin jäsen), Wagner, P. (Projektin jäsen) & Kiefer, A. (Projektin jäsen)
01/09/2016 → 31/03/2021
Projekti: Academy of Finland: Other research funding

Biotalousinfrastruktuuri
Seppälä, J. (Manager)
Kemian tekniikan korkeakoulu
Laitteistot/tilat: Facility

Siteeraa tätä

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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",

publisher = "Royal Society of Chemistry",

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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

SN - 1463-9262

VL - 19

SP - 447

EP - 452

JO - Green Chemistry

JF - Green Chemistry

ER -

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

Abstrakti

Pääsy asiakirjaan

Sormenjälki

Projektit

Enzymer som katalysatorer i icke-naturliga syntetiska transformationer

Laitteet

Biotalousinfrastruktuuri

Siteeraa tätä