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Lipase-Induced Oxidative Furan Rearrangements

Fabian Blume, Petra Sprengart, Jan Deska

*Department of Chemistry & Materials Science, Aalto-yliopisto, Kemistintie 1, 02150 Espoo, Finland, Email: jan.deskaaalto.fi

F. Blume, P. Sprengart, J. Deska, Synlett, 2018, 29, 1293-1296.

DOI: 10.1055/s-0036-1591889 (free Supporting Information)



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Abstract

Lipase B from Candida antarctica catalyzes the oxidative ring expansion of furfuryl alcohols in the presence of aqueous hydrogen peroxide to yield functionalized pyranones under mild conditions. The corresponding piperidinone derivatives can be obtained by a similar enzymatic rearrangement of N-protected furfurylamines.

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Key Words

Achmatowicz, ring expansion, furans, pyranones, oxygen heteroycles, lactols, hydrogen peroxide, synthetic methodology, heterocyclic chemistry.


ID: J60-Y2018