title: 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.
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.
authors.affiliation: Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstraße 30, D-70599 Stuttgart, Germany.
authors.forename: Chimène
authors.initials: C
authors.lastname: Asta
authors.forename: Dietmar
authors.initials: D
authors.lastname: Schmidt
authors.forename: Jürgen
authors.initials: J
authors.lastname: Conrad
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Frey
authors.forename: Uwe
authors.initials: U
authors.lastname: Beifuss
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000737:chemistry* / Q000378:metabolism; D042845:Laccase / Q000737:chemistry* / Q000378:metabolism; D058116:Lewis Acids / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D001572:Benzofurans; D003512:Cyclohexanones; D005663:Furans; D058116:Lewis Acids; C004636:1,3-cyclohexanedione; C037555:2,5-dimethylfuran; D042845:Laccase