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Analysis of institutional authors

Wong, Thomas Hin-FungAuthor

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May 15, 2023
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Article

Stereoselective conjugate cyanation of enals by combining photoredox and organocatalysis

Publicated to: Nature Catalysis. 6 (4): 332-338 - 2023-04-06 6(4), DOI: 10.1038/s41929-023-00939-y

Authors:

Berger, M; Ma, D; Baumgartner, Y; Wong, THF; Melchiorre, P
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Affiliations

Barcelona Inst Sci & Technol, Inst Chem Res Catalonia, ICIQ, Tarragona, Spain - Author
Univ Bologna, Dept Ind Chem Toso Montanari, Bologna, Italy - Author

Abstract

Precise control over the selectivity of a reaction is a fundamental target. While great advances have been obtained in achieving stereocontrol, the selective manipulation of functional groups within a substrate (chemoselectivity) is still a challenge. The cyanation of aldehydes offers an illustrative example: the 1,2-addition of nucleophilic cyanide to the aldehydic group was one of the first examples of a stereoselective catalytic process. By contrast, the conjugate cyanation of linear alpha,beta-unsaturated aldehydes has remained elusive, even in a racemic variant. The main difficulty lies in achieving 1,4-chemoselectivity over the preferred cyanide 1,2-addition. Here, we report an asymmetric catalytic method to achieve the exclusive conjugate cyanation of enals. The synergistic action of a chiral organocatalyst with a visible-light-activated photoredox catalyst promotes the single-electron reduction of enals, inducing a formal inversion of polarity. The resulting chiral radical, being nucleophilic in character, is then intercepted by an electrophilic cyanide source with p-er-fe-ct 1-,4-chemoselectivity and good stereocontrol.
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Keywords

AldehydesBeta-alkylationCatalysisCyanideCyanosilylationHydrocyanationInventionKetones

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Nature Catalysis 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 1/178, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Physical. 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: 2.11. 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 2026-01-21, the following number of citations:

  • WoS: 21
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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 2026-01-21:

  • 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: 33.
  • 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: 33 (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: 20.
  • The number of mentions on the social network X (formerly Twitter): 34 (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.
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Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: Italy.

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 (Berger, Martin) .

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Awards linked to the item

Financial support was provided by the Ministry for Science and Innovation AEI/10.13039/501100011033 (CEX2019-000925-S) and Agencia Estatal de Investigacion (PID2019-106278GB-I00). M.B. thanks the Austrian Science Foundation (FWF, J4603-N) for an Erwin-Schroedinger postdoctoral fellowship. Y.B. thanks the Swiss National Science Foundation (P2BSP2_200098) for a postdoctoral fellowship. D.M. thanks the European Union for a Horizon 2020 Marie Sklodowska-Curie Fellowship (H2020-MSCA-IF-2019 894795). T.H.-F.W. thanks the Government of Catalonia for an FI Fellowship (2021FI-B00304). We thank P. Capurro for preliminary investigations, M. Martinez and J. Benet for X-ray crystallographic analysis and M. Gimenez and C. Rivero for assistance with ozonolysis and hydrogenation experiments.
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