Combination of Enzyme- and Lewis Acid-Catalyzed Reactions: A New Method for the Synthesis of 6,7-Dihydrobenzofuran-4(5H)-ones Starting from 2,5-Dimethylfuran and 1,3-Cyclohexanediones

Publication Type
Journal contribution (peer reviewed)
Authors
Asta, C.; Schmidt, D.; Conrad, J.; Frey, W.; Beifuss, U.
Year of publication
2013
Published in
Org. Biomol. Chem.
Band/Volume
11/
DOI
10.1039/C3OB40926K
Page (from - to)
5692-5701
Abstract

The Lewis acid-catalyzed domino 1,2-addition/1,4-addition/elimination between (Z)-3-hexene-2,5-dione and 1,3-dicarbonyls delivers 3-methyl-6,7-dihydrobenzofuran-4(5H)-ones exclusively with yields up to 82%. The combination of this new process with the laccase-catalyzed formation of (Z)-3-hexene-2,5-dione by oxidative cleavage of 2,5-dimethylfuran allows for the synthesis of 6,7-dihydrobenzofuran-4(5H)-ones starting directly from 2,5-dimethylfuran.

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