Issue 2, 2017

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 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

Supplementary files

Article information

Article type
Paper
Submitted
14 7 2016
Accepted
09 9 2016
First published
09 9 2016
This article is Open Access
Creative Commons BY license

Green Chem., 2017,19, 447-452

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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