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Analysis of institutional authors

Cataffo, AAuthorEchavarren, AmCorresponding Author

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January 3, 2024
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Article

Chiral Auxiliary Approach for Gold(I)-Catalyzed Cyclizations

Publicated to: Angewandte Chemie (International Ed. Print). 62 (49): e202312874-- - 2023-12-04 62(49), DOI: 10.1002/anie.202312874

Authors:

Cataffo, A; Pena-Lopez, M; Pedrazzani, R; Echavarren, AM
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Affiliations

Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ Cerca, Av Paisos Catalans 16, Tarragona 43007, Spain - Author
Univ Rovira i Virgili, Dept Quim Analit & Quim Organ, C-Marcelli Domingo S-N, Tarragona 43007, Spain - Author

Abstract

Two different classes of stereoselective cyclizations have been developed using a chiral auxiliary approach with commercially available [JohnPhosAu(MeCN)SbF6] as catalyst. First, a stereoselective cascade cyclization of 1,5-enynes was achieved using the Oppolzer camphorsultam as chiral auxiliary. In this case, a one-pot cyclization-hydrolysis sequence was developed to directly afford enantioenriched spirocyclic ketones. Then, the stereoselective alkoxycyclization of 1,6-enynes was mediated by an Evans-type oxazolidinone. A reduction-hydrolysis sequence was selected to remove the auxiliary to give enantioenriched beta-tetralones. DFT studies confirmed that the steric clash between the chiral auxiliary and alkene accounts for the experimentally observed diastereoselective cyclization through the Si face. The stereoselective gold(I)-catalyzed cascade cyclization of 1,5-enynes and alkoxycyclization of 1,6-enynes with chiral auxiliaries has been developed, affording, after hydrolysis, synthetically challenging enantioenriched ketones. This chiral auxiliary approach is an alternative to the use of complex chiral catalysts in gold(I)-catalyzed asymmetric cyclizations.image
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Keywords

alkoxycyclizationchiral auxiliariesenynesgold catalysisAlkenesAlkoxycyclizationAlkynesC-nCatalyzed reactionChiral auxiliariesCycloisomerizationsEnantioselective constructionEnynesGold catalysisIntermolecular 2+2 cycloadditionRearrangementSpirocyclic ketonesUnique

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 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, 2023, it was in position 14/231, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Multidisciplinary. Notably, the journal is positioned above the 90th percentile.

From a relative perspective, and based on the normalized impact indicator calculated from World Citations provided by WoS (ESI, Clarivate), it yields a value for the citation normalization relative to the expected citation rate of: 1.14. This indicates that, compared to works in the same discipline and in the same year of publication, it ranks as a work cited above average. (source consulted: ESI Nov 13, 2025)

Specifically, and according to different indexing agencies, this work has accumulated citations as of 2026-04-07, the following number of citations:

  • WoS: 10
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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 2026-04-07:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 14.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 14 (PlumX).

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: 7.
  • The number of mentions on the social network X (formerly Twitter): 13 (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.
  • Assignment of a Handle/URN as an identifier within the deposit in the Institutional Repository: http://hdl.handle.net/2072/537010
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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: First Author (Cattafo, Andrea) and Last Author (Echavarren Pablos, Antonio M.).

the author responsible for correspondence tasks has been Echavarren Pablos, Antonio M..

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Awards linked to the item

We thank the MCIN/AEI/10.13039/501100011033 (PID2022-136623NB-I00, and CEX2019-000925-S), the European Research Council (Advanced Grant 835080), the AGAUR (2021 SGR 01256), and CERCA Program/Generalitat de Catalunya for financial support. We thank Zhouting Rong for his results on enantioselective polyenyne cyclizations, which were the basis to develop the current work. We also thank ICIQ X-ray diffraction, NMR, and mass spectrometry units.
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