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Peer-reviewedCC BYOrganic letters

Asymmetric Access to Structurally Complex 1-Tetralols through Diels-Alder Cycloadditions of Photogenerated Hydroxy-o-quinodimethanes and Acrylates.

  • María González-Marcos1
  • José Trujillo-Sierra1
  • Enara Esteban1
  • José M Sansano1
  • Ana Sirvent1
  • María de Gracia Retamosa1
  1. 1Departamento de Química Orgánica/Institute of Organic Synthesis and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, 03080-Alicante, Spain.
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Abstract

Photoenolization/Diels-Alder (PEDA) reactions provide a rapid approach to highly substituted 1-tetralols. Herein, we report a PEDA strategy using activated acrylate-based dienophiles for the synthesis of densely functionalized 1-tetralols with high diastereoselectivity. Isatin-derived acrylates enable access to spirocyclic architectures, while chiral auxiliary-based acrylates allow an asymmetric variant, providing enantioenriched 1-tetralol derivatives with efficient stereocontrol.

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Cite

BibTeXRIS
BibTeX
@article{gonzalezmarcos2026asymmetric,
  title = {{Asymmetric Access to Structurally Complex 1-Tetralols through Diels-Alder Cycloadditions of Photogenerated Hydroxy-o-quinodimethanes and Acrylates.}},
  author = {María González-Marcos and José Trujillo-Sierra and Enara Esteban and José M Sansano and Ana Sirvent and María de Gracia Retamosa},
  journal = {Organic letters},
  year = {2026},
  month = sep,
  doi = {10.1021/acs.orglett.6c03349},
  url = {https://europepmc.org/article/MED/42918043},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Asymmetric Access to Structurally Complex 1-Tetralols through Diels-Alder Cycloadditions of Photogenerated Hydroxy-o-quinodimethanes and Acrylates.
AU  - María González-Marcos
AU  - José Trujillo-Sierra
AU  - Enara Esteban
AU  - José M Sansano
AU  - Ana Sirvent
AU  - María de Gracia Retamosa
PY  - 2026
DA  - 2026/09/01
JO  - Organic letters
DO  - 10.1021/acs.orglett.6c03349
UR  - https://europepmc.org/article/MED/42918043
AB  - Photoenolization/Diels-Alder (PEDA) reactions provide a rapid approach to highly substituted 1-tetralols. Herein, we report a PEDA strategy using activated acrylate-based dienophiles for the synthesis of densely functionalized 1-tetralols with high diastereoselectivity. Isatin-derived acrylates enable access to spirocyclic architectures, while chiral auxiliary-based acrylates allow an asymmetric variant, providing enantioenriched 1-tetralol derivatives with efficient stereocontrol.
SN  - 1523-7060
SN  - 1523-7052
ER  -