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Duality of Donor–Acceptor Cyclopropane Reactivity as a Three‐Carbon Component in Five‐Membered Ring Construction: [3+2] Annulation Versus [3+2] Cycloaddition
Author(s) -
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.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300731
Subject(s) - annulation , cyclopropane , chemistry , ring (chemistry) , reactivity (psychology) , cycloaddition , lewis acids and bases , stereochemistry , acceptor , carbon fibers , aryl , medicinal chemistry , catalysis , organic chemistry , mathematics , physics , pathology , algorithm , composite number , condensed matter physics , medicine , alternative medicine , alkyl
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 IC 50 of 10 −6 –10 −5 M .