title: Direct synthesis of benzofuro[2,3-b]pyrroles through a radical addition/[3,3]-sigmatropic rearrangement/cyclization/lactamization cascade.
abstract: A straightforward synthetic method for the construction of benzofuro[2,3-b]pyrrol-2-ones by a novel domino reaction through a radical addition/[3,3]-sigmatropic rearrangement/cyclization/lactamization cascade has been developed. The domino reaction of O-phenyl-conjugated oxime ether with an alkyl radical allows the construction of two heterocycles with three stereogenic centers as a result of the formation of two C-C bonds, a C-O bond, and a C-N bond in a single operation, leading to pyrrolidine-fused dihydrobenzofurans, which are not easily accessible by existing synthetic methods. Furthermore, asymmetric synthesis of benzofuro[2,3-b]pyrrol-2-one derivatives through a diastereoselective radical addition reaction to a chiral oxime ether was also developed.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558 (Japan), Fax: (+81)78-441-7554.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ueda
authors.forename: Yuta
authors.initials: Y
authors.lastname: Ito
authors.forename: Yuki
authors.initials: Y
authors.lastname: Ichii
authors.forename: Maiko
authors.initials: M
authors.lastname: Kakiuchi
authors.forename: Hiroko
authors.initials: H
authors.lastname: Shono
authors.forename: Okiko
authors.initials: O
authors.lastname: Miyata
mesh_terms: D001572:Benzofurans / Q000737:chemistry; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D005609:Free Radicals; D010091:Oximes; D011758:Pyrroles; D011759:Pyrrolidines; C032519:pyrrolidine; C105430:benzofuran
keywords: domino reaction; heterocycles; radical reactions; rearrangement; synthetic methods