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March 6, 2023
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Base-induced sulfoxide-sulfenate rearrangement of 2-sulfinyl dienes for the regio- and stereoselective synthesis of enantioenriched dienyl diols

Publicated to: JOURNAL OF ORGANIC CHEMISTRY. 88 (6): 3697-3713 - 2023-03-17 88(6), DOI: 10.1021/acs.joc.2c02931

Authors: Velado, M.; Martinovic, M.; Alonso, I.; Tortosa, M.; de la Pradilla, R.F.; Viso, A.

Affiliations

CSIC, Inst Quim Organ Gen IQOG, Madrid 28006, Spain - Author
Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid (UAM), 28049 Madrid, Spain. - Author
Univ Autonoma Madrid UAM, Ctr Innovat Adv Chem ORFEO CINQA, Madrid 28049, Spain - Author
Univ Autonoma Madrid UAM, Inst Adv Res Chem Sci IAdChem, Madrid 28049, Spain - Author
Univ Autonoma Madrid UAM, Organ Chem Dept, Madrid 28049, Spain - Author
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Abstract

The base-induced [2,3]-sigmatropic rearrangement of a series of enantiopure 2-sulfinyl dienes has been examined and optimized using a combination of NaH and iPrOH. The reaction takes place by allylic deprotonation of the 2-sulfinyl diene to give a bis-allylic sulfoxide anion intermediate that after protonation undergoes sulfoxide-sulfenate rearrangement. Different substitution at the starting 2-sulfinyl dienes has allowed us to study the rearrangement finding that a terminal allylic alcohol is determinant to achieve complete regioselectivity and high enantioselectivities (90:10-95:5) with the sulfoxide as the only element of stereocontrol. Density functional theory (DFT) calculations provide an interpretation of these results.

Keywords

alcoholsMislow-evans rearrangement

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal JOURNAL OF ORGANIC CHEMISTRY 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 10/58, thus managing to position itself as a Q1 (Primer Cuartil), in the category Chemistry, Organic.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2025-12-11:

  • Scopus: 1

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 2025-12-11:

  • 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: 4 (PlumX).

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:

Awards linked to the item

The authors thank MICINN (PID2019-107380GB-I00) for financial support. M.M. thanks Erasmus+ program for an internship. The authors thank Paula Lopez and Fernando Romero for their initial experiments with compounds 8, 9, and 11. They also thank the Centro de Computacion Cientifica at the UAM for their generous allocation of computer time.