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Issue 2, 2017
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Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles

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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 diastereo- and enantioenriched allenes remains uncompromised and chiral dihydrofurans can be obtained via 5-endo-trig cyclizations with perfect axis-to-centre chirality transfer.

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

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Supplementary files

Article information


Submitted
14 Jul 2016
Accepted
09 Sep 2016
First published
09 Sep 2016

This article is Open Access

Green Chem., 2017,19, 447-452
Article type
Paper

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

J. Naapuri, J. D. Rolfes, J. Keil, C. Manzuna Sapu and J. Deska, Green Chem., 2017, 19, 447
DOI: 10.1039/C6GC01926A

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