PDF icon Download PDF
Synthesis
DOI: 10.1055/a-2705-5720
Paper

GaCl3-catalyzed cascade cyclization of 2-arylcyclopropane-1,1-dicarboxylates as 1,3-zwitterions with 3-arylbuta-1,2-dienes

Anastasiya A Ershova
1   Chemistry Department, Lomonosov Moscow State University Faculty of Chemistry, Moscow, Russian Federation (Ringgold ID: RIN204326)
2   Laboratory 6, FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Elizaveta A Ulchenko
3   Department of Biomedical Products, Dmitry Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation (Ringgold ID: RIN65054)
2   Laboratory 6, FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Denis Dmitrievich Borisov
4   Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation
,
Ekaterina Budynina
5   Chemistry, Moscow State University, Moscow, Russian Federation
,
Roman A. Novikov
4   Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation
,
Yury V. Tomilov
4   Russian Academy of Sciences, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation
› Author Affiliations
Supported by: Russian Science Foundation 22-13-00418-P
› Further Information
 PDF Download All articles of this category
Preview

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.



Publication History

Received: 23 June 2025

Accepted after revision: 02 September 2025

Accepted Manuscript online:
19 September 2025

© . Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany