Chemical Review and Letters

Enantioselective alkynylation of cyclopentanone: Synthesis, dimerization, and cross-coupling transformations of 1-ethynylcyclopentan-1-ol

Document Type : Research Article

Authors

Guzal Otamukhamedova 1
Odiljon Ziyadullaev 2
Forxod Buriev 3
Lochinbek Ablakulov 3
Jonibek Khayitov 4

1 Department of Scientific Research, Innovations and Scientific-Pedagogical Personnel Training, Chirchik State Pedagogical University, P. O. Box: 111700, Chirchik, Uzbekistan.

2 Department of Pedagogy and Psychology, Alfraganus University, P. O. Box: 100190, Tashkent, Uzbekistan.

3 Department of Chemistry, Chirchik State Pedagogical University, Chirchik, Uzbekistan.

4 Department of Oil and Gas Engineering and Processing Technologies, Karshi State Technical University, P. O. Box: 180100, Karshi, Uzbekistan.

https://doi.org/10.22034/crl.2025.544888.1688
Abstract
In the present investigation, the preparation of 1-ethynylcyclopentan-1-ol was carried out via the enantioselective alkynylation of cyclopentanone using a Zn(OTf)₂/TBAF·3H₂O complex catalytic system. Тhe process was carried out in acetonitrile (MeCN) medium for 120 minutes at –10 °C. The molar ratio of acetylene to cyclopentanone was adjusted to 2:1, while the combined loading of the catalytic system Zn(OTf)2/TBAF·3H2O was maintained at 0.05 mol with respect to the starting materials. Furthermore, its subsequent oxidative homolytic dimerization and Sonogashira-type C–C cross-coupling reaction with benzyl chloride were explored. A comprehensive study was performed on various parameters affecting the formation process and the efficiency of acetylene alcohol derivatives, such as temperature regime, reaction time, catalytic composition and solvent polarity, stoichiometric ratios of reagents and substrates, as well as the identity and proportion of transient intermediates and side-products. Based on the acquired experimental data, the optimal conditions for the nucleophilic addition–coupling pathway were established, and the plausible reaction mechanisms were proposed. The obtained compounds were thoroughly characterized, and their equilibrium constants, molecular structures, purity levels, and chemical composition were verified using modern physicochemical analysis techniques.

Graphical Abstract

Enantioselective alkynylation of cyclopentanone: Synthesis, dimerization, and cross-coupling transformations of 1-ethynylcyclopentan-1-ol

Keywords

acetylene alcohol
dimerization
сross-coupling reaction
reaction mechanism
product yield

Subjects

Chemical Review and Letters
Volume 9, Issue 1 - Serial Number 1
January and February 2026
Pages 192-200

  • Receive Date 04 September 2025
  • Revise Date 11 November 2025
  • Accept Date 12 November 2025

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