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DOI: 10.1055/a-2705-5720
GaCl3-catalyzed Cascade Cyclization of 2-Arylcyclopropane-1,1-dicarboxylates as 1,3-Zwitterions with 3-Arylbuta-1,2-dienes
Authors
Supported by: Russian Science Foundation 22-13-00418-P
Funding Information This work was funded by the Russian Science Foundation (grant no. 22-13-00418-P).
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.
Keywords
Donor–acceptor cyclopropanes - Allenes - Cyclization reaction - Lewis acids - Gallium trichloridePublication History
Received: 23 June 2025
Accepted after revision: 02 September 2025
Accepted Manuscript online:
19 September 2025
Article published online:
23 October 2025
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