title: Silver-catalyzed asymmetric synthesis of 2,3-dihydrobenzofurans: a new chiral synthesis of pterocarpans.
abstract: 2,3-Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3-dihydrobenzoxasilepines under the catalysis of Ag(I) complexes, and in the presence of a source of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis-pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (-)-pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5-dihydrobenzoxepine is also presented.
authors.affiliation: Departamento de Química Orgánica, Universidad de Almería, 04120 Almería, Spain.
authors.forename: Leticia
authors.initials: L
authors.lastname: Jiménez-González
authors.forename: Sergio
authors.initials: S
authors.lastname: García-Muñoz
authors.forename: Miriam
authors.initials: M
authors.lastname: Alvarez-Corral
authors.forename: Manuel
authors.initials: M
authors.lastname: Muñoz-Dorado
authors.forename: Ignacio
authors.initials: I
authors.lastname: Rodríguez-García
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis*; D002384:Catalysis; D008956:Models, Chemical; D036343:Pterocarpans / Q000138:chemical synthesis*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D036343:Pterocarpans; D012834:Silver; C043168:coumaran