Duality of donor-acceptor cyclopropane reactivity as a three-carbon component in five-membered ring construction: [3+2] annulation versus [3+2] cycloaddition

Yulia A Volkova; Ekaterina M Budynina; Alexey E Kaplun; Olga A Ivanova; Alexey O Chagarovskiy; Dmitriy A Skvortsov; Victor B Rybakov; Igor V Trushkov; Mikhail Ya Melnikov

doi:10.1002/chem.201300731

Duality of donor-acceptor cyclopropane reactivity as a three-carbon component in five-membered ring construction: [3+2] annulation versus [3+2] cycloaddition

Chemistry. 2013 May 17;19(21):6586-90. doi: 10.1002/chem.201300731. Epub 2013 Apr 9.

Authors

Yulia A Volkova¹, Ekaterina M Budynina, Alexey E Kaplun, Olga A Ivanova, Alexey O Chagarovskiy, Dmitriy A Skvortsov, Victor B Rybakov, Igor V Trushkov, Mikhail Ya Melnikov

Affiliation

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russia.

PMID: 23576404
DOI: 10.1002/chem.201300731

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry
Carbon
Catalysis
Cycloaddition Reaction
Cyclopropanes / chemical synthesis
Cyclopropanes / chemistry*
Cyclopropanes / pharmacology
Humans
Lewis Acids / chemistry*
Molecular Structure
Stereoisomerism

Substances

Alkenes
Cyclopropanes
Lewis Acids
Carbon