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GaCl3-catalyzed Cascade Cyclization of 2-Arylcyclopropane-1,1-dicarboxylates as 1,3-Zwitterions with 3-Arylbuta-1,2-dienes Full article

Journal Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881
Output data Year: 2025, Volume: 57, Number: 24, Pages: 3685-3691 Pages count : 7 DOI: 10.1055/a-2705-5720
Authors Ershova Anastasiya A 1,2 , Ulchenko Elizaveta A 3,2 , Borisov Denis Dmitrievich 2 , Budynina Ekaterina 1 , Novikov Roman A. 2 , Tomilov Yury V. 2
Affiliations
1 Chemistry Department, Lomonosov Moscow State University Faculty of Chemistry, Moscow, Russian Federation
2 FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation
3 Department of Biomedical Products, Dmitry Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: The cascade cyclization of 2-arylcyclopropane-1,1-dicarboxylates (ACDС) with 3-arylbuta-1,2-dienes in the presence of 2-2.5 equiv GaCl3 under the conditions for generation of 1,3-zwitter-ion intermediates was studied. The reaction yielded substituted 3,3a,8,8a-tetrahydrocyclopenta[a]indenes exclusively as cis,trans isomers in yields of up to 75%. This reaction was implemented both as a one-pot process and in a two-step variant with isolation of the primary cyclization products, namely, the corresponding methylidene cyclopentane-1,1-dicarboxylates. It was shown that the course of the reaction is strongly affected by the electronic effects of substituents in the aromatic moieties of ACDC and allenes.
Cite: Ershova A.A. , Ulchenko E.A. , Borisov D.D. , Budynina E. , Novikov R.A. , Tomilov Y.V.
GaCl3-catalyzed Cascade Cyclization of 2-Arylcyclopropane-1,1-dicarboxylates as 1,3-Zwitterions with 3-Arylbuta-1,2-dienes
Synthesis-Stuttgart. 2025. V.57. N24. P.3685-3691. DOI: 10.1055/a-2705-5720 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001600109300001
≡ Scopus: 2-s2.0-105020395553
≡ OpenAlex: W4414346434
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