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 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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Original languageEnglish
Pages (from-to)447-452
Number of pages6
JournalGreen Chemistry
Volume19
Publication statusPublished - 2017
MoE publication typeA1 Journal article-refereed

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ID: 10701927