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July 31, 2025
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Article

Terpene cyclization catalysis with a functional cavitand: driving selectivity through precise molecular recognition

Publicated to: Organic Chemistry Frontiers. 12 (21): 5985-5991 - 2025-07-15 12(21), DOI: 10.1039/d5qo00922g

Authors: Lopez-Coll, Ricard; Lledo, Agusti

Affiliations

Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Ave Paisos Catalans 16, Tarragona 43007, Spain - Author
Univ Girona, Inst Quim Computac & Catalisi IQCC, Maria Aurelia Capmany 69, Girona 17003, Spain - Author

Abstract

A three-walled self-folding cavitand receptor derived from resorcin[4]arene featuring phenol groups near the confined space catalyzes the cyclization reaction of nerol, using HCl as co-catalyst. In contrast to terpene cyclization reactions mediated by other synthetic hosts, the process reported herein is substrate specific, provides very high selectivity towards cyclization products, and delivers limonene-a thermodynamically disfavored product-as the major compound. The observed acceleration, turnover and unique selectivity are rationalized on the basis of precise molecular recognition phenomena, supported by NMR studies and DFT calculations.

Keywords

Aza analogsBindinDeep cavitandInhibitionOrganocatalysisReceptorWater

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Organic Chemistry Frontiers due to its progression and the good impact it has achieved in recent years, according to the agency WoS (JCR), it has become a reference in its field. In the year of publication of the work, 2025, it was in position 5/57, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic. Notably, the journal is positioned above the 90th percentile.

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-13:

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 10.
  • The number of mentions on the social network X (formerly Twitter): 10 (Altmetric).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.

Leadership analysis of institutional authors

There is a significant leadership presence as some of the institution’s authors appear as the first or last signer, detailed as follows: Last Author (Lledo, Agusti).

the author responsible for correspondence tasks has been Lledo, Agusti.

Awards linked to the item

We are grateful for financial support from grants PID2020-113181GB-I00, PID2023-146498NB-I00, and REQ2021_B_05 funded by MICIU/AEI/10.13039/501100011033. We thank AGAUR/Generalitat de Catalunya for funding (2021SGR623) and for a pre-doctoral fellowship to R. L. (2020 FI_B 00132). Open Access funding provided thanks to the CRUE-CSIC agreement with the RSC.