title: Duality of donor-acceptor cyclopropane reactivity as a three-carbon component in five-membered ring construction: [3+2] annulation versus [3+2] cycloaddition.
abstract: Quo vadis? The Lewis acid catalyzed reaction of (hetero)aryl-derived donor-acceptor cyclopropanes with alkenes can be selectively directed along a [3+2] annulation pathway (see scheme). This new process provides convenient and efficient access to indanes and other cyclopentannulated (hetero)arenes, among which polyoxygenated 1-arylindanes exhibit significant cytotoxicity against several cancer cell lines with an IC50 of 10(-6)-10(-5)  M.
authors.affiliation: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russia.
authors.forename: Yulia A
authors.initials: YA
authors.lastname: Volkova
authors.forename: Ekaterina M
authors.initials: EM
authors.lastname: Budynina
authors.forename: Alexey E
authors.initials: AE
authors.lastname: Kaplun
authors.forename: Olga A
authors.initials: OA
authors.lastname: Ivanova
authors.forename: Alexey O
authors.initials: AO
authors.lastname: Chagarovskiy
authors.forename: Dmitriy A
authors.initials: DA
authors.lastname: Skvortsov
authors.forename: Victor B
authors.initials: VB
authors.lastname: Rybakov
authors.forename: Igor V
authors.initials: IV
authors.lastname: Trushkov
authors.forename: Mikhail Ya
authors.initials: MY
authors.lastname: Melnikov
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002244:Carbon; D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003521:Cyclopropanes; D058116:Lewis Acids; D002244:Carbon