Journal Articles Journal of Organic Chemistry Year : 2025

Construction of thiochroman-4-ols through a (4 + 2) annulation strategy using allenyl sulfones as substrates

Abstract

Herein, we report an efficient and straightforward access to highly functionalized thiochroman-4-ol derivatives by the construction of S−C and C−C bonds in a domino fashion. The methodology is based on a (4 + 2) annulation reaction involving α- substituted allenyl sulfones and aromatic thiolates displaying an ortho α-ketoester group as substrates. The anionic sulfur species were generated in situ by reduction of the corresponding disulfides, using a Rongalite/K2CO3 system. The practicality of the strategy was further demonstrated by gram-scale synthesis, postmodifications, and compatibility with other types of electron-deficient allenes (allenoate and allenone).

Fichier principal
Vignette du fichier
Perrio-joc-2025-00212t-revised2.pdf (2.91 Mo) Télécharger le fichier
Origin Files produced by the author(s)
Licence

Dates and versions

hal-05085627 , version 1 (07-11-2025)

Licence

Identifiers

Cite

Lilia Anani, Jean-François Lohier, Annie-Claude Gaumont, Jean-François Brière, Sylvain Oudeyer, et al.. Construction of thiochroman-4-ols through a (4 + 2) annulation strategy using allenyl sulfones as substrates. Journal of Organic Chemistry, 2025, 90 (16), pp.5538-5545. ⟨10.1021/acs.joc.5c00212⟩. ⟨hal-05085627⟩
234 View
144 Download

Altmetric

Share

  • More