Straightforward synthesis of enantiopure 2,3-dihydrobenzofurans by a sequential stereoselective biotransformation and chemical intramolecular cyclization.
A new family of optically active 2,3-dihydrobenzofurans has been prepared by a simple chemoenzymatic asymmetric strategy. This synthetic approach is based on the combination of a lipase-mediated kinetic resolution of 1-aryl-2-propanols or bioreduction of the corresponding ketones followed by an intramolecular cyclization reaction. These novel compounds have been prepared in enantiopure form and in good overall yield through a straightforward route.
Mangas-Sánchez
Juan
J
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33006 Spain.
Busto
Eduardo
E
Gotor-Fernández
Vicente
V
Gotor
Vicente
V
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001711:Biotransformation; D016956:Burkholderia cepacia / Q000201:enzymology; D002384:Catalysis; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*
D001572:Benzofurans; D006846:Hydrocarbons, Halogenated; D020005:Propanols; D008049:Lipase