Duality of Donor–Acceptor Cyclopropane Reactivity as a Three‐Carbon Component in Five‐Membered Ring Construction: [3+2] Annulation Versus [3+2] Cycloaddition. Issue 21 (9th April 2013)

• Record Type: Journal Article
• Authors: Volkova, Yulia A.; Budynina, Ekaterina M.; Kaplun, Alexey E.; Ivanova, Olga A.; Chagarovskiy, Alexey O.; Skvortsov, Dmitriy A.; Rybakov, Victor B.; Trushkov, Igor V.; Melnikov, Mikhail Ya.
• Is Part Of: Chemistry. Volume 19:Issue 21(2013)
• Page Start: 6586
• Page End: 6590
• Publication Date: 2013-04-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201300731
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Quo vadis?</bold> 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 <sc>M</sc>.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1ztbfhwr" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>