Synlett 2025; 36(01): 69-74
DOI: 10.1055/a-2330-0819
letter

Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

Ryuichi Murata
a   Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
,
Rakuto Yoshida
b   Institute for Catalysis, Hokkaido University, Sapporo, Hokkaido 001-0021, Japan
,
b   Institute for Catalysis, Hokkaido University, Sapporo, Hokkaido 001-0021, Japan
c   List Sustainable Digital Transformation Catalyst Collaboration Research Platform, Institute for Chemical Reaction Design and Discovery (ICReDD List-PF), Hokkaido University, Sapporo, Hokkaido 001-0021, Japan
,
Keisuke Asano
b   Institute for Catalysis, Hokkaido University, Sapporo, Hokkaido 001-0021, Japan
› Author Affiliations
This work was supported financially by the Japanese Ministry of Education, Culture, Sports, Science and Technology (JP21H05076, JP23H01953, and JP23K26646). K.A. also acknowledges the Inoue Foundation for Science, the Mizuho Foundation for the Promotion of Sciences, the Japan Association for Chemical Innovation, the Tobe Maki Scholarship Foundation, the NOVARTIS Foundation (Japan) for the Promotion of Science, a Kurata Grants from the Hitachi Global Foundation, the Inamori Foundation, and the Society of Iodine Science. R.M. also acknowledges the Japan Society for the Promotion of Science for Young Scientists for a fellowship support (JP21J23149).


Abstract

Cross-coupling methods for the introduction of various substituents onto the olefin moiety of cyclooctenes were developed. A range of 1-substituted cis-cyclooctenes were synthesized. These protocols unlocked routes to previously inaccessible derivatives, permitting the syntheses of cis-cyclooctenes bearing various functional groups. Moreover, the method was applied to the synthesis of a 1,2-disubstituted trans-cyclooctene for the first time, which proved to be a significantly more active organocatalyst than the previously developed monosubstituted trans-cyclooctene.

Supporting Information



Publication History

Received: 18 April 2024

Accepted after revision: 18 May 2024

Accepted Manuscript online:
18 May 2024

Article published online:
03 June 2024

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