Organocatalytic Strategy for a Formal 1,6-Conjugate Hydroxylation
Thanks to the versatile vinylogous hexafluoro <i>iso</i>-propyl acrylate molecular platforms, a regio- and enantioselective sulfa-Michael reaction was achieved upon organocatalytic conditions, allowing the subsequent amidation, one-pot oxidation, and Mislow-Bravermann-Evans [2,3]-sigmatropic rearrangement along with a 1,3-chirality transfer, leading eventually to a formal asymmetric 1,6-hydroxylation sequence.
Authors
- Vincent Levacher (ORCID: https://orcid.org/0000-0002-6429-1965)
- Stéphane Perrio (ORCID: https://orcid.org/0000-0002-3371-2405)
- Jean‐Valère Naubron (ORCID: https://orcid.org/0000-0002-8523-4476)
- Sylvain Oudeyer (ORCID: https://orcid.org/0000-0001-8238-800X)
- Nicolas Vanthuyne (ORCID: https://orcid.org/0000-0003-2598-7940)
- Jean‐François Brière (ORCID: https://orcid.org/0000-0002-1381-4535)
- Anthony Lapray (ORCID: https://orcid.org/0009-0005-5081-7769)
- Sifeddine Mohamed Aouina
Institutions
- Centre National de la Recherche Scientifique (FR)
- École Nationale Supérieure d'Ingénieurs de Caen (FR)
- Normandie Université (FR)
- Centrale Méditerranée (FR)
- Laboratoire COBRA (FR)
- Université de Rouen Normandie (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
- Université de Caen Normandie (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-18
- DOI
- https://doi.org/10.1021/acs.orglett.4c03482
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Indian National Science Academy
- Agence Nationale de la Recherche
- Centre National de la Recherche Scientifique
- Université de Rouen
- Institut National des Sciences Appliquées Rouen
- Institut Carnot Santé Animale
- European Regional Development Fund