Phenolic Dienes as Highly Selective Dienophiles in the Asymmetric Organocatalyzed Three-Component Vinylogous Povarov Reaction.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
17 Aug 2024
Historique:
medline: 17 8 2024
pubmed: 17 8 2024
entrez: 17 8 2024
Statut: aheadofprint

Résumé

Our study presents a novel enantioselective route for the synthesis of 1,2,3,4-tetrahydroquinolines via a chiral phosphoric acid-catalyzed three-component Povarov reaction, employing phenolic dienes as dienophiles. This approach produces a diverse array of 2,3,4-trisubstituted tetrahydroquinolines, each featuring a styryl group at position 4, in high yields with excellent regio-, diastereo-, and enantioselectivities (>95:5 dr and up to >99% ee).

Identifiants

pubmed: 39152912
doi: 10.1021/acs.joc.4c01239
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Auteurs

Aurélien Brion (A)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.

Vittoria Martini (V)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
SynCat Lab, Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, 43124 Parma, Italy.

Marine Lombard (M)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.

Pascal Retailleau (P)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.

Nicola Della Ca' (N)

SynCat Lab, Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, 43124 Parma, Italy.

Luc Neuville (L)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
HitCat, Seqens-CNRS Joint Laboratory, Seqens'Lab, 8 Rue de Rouen, 78440 Porcheville, France.

Géraldine Masson (G)

Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
HitCat, Seqens-CNRS Joint Laboratory, Seqens'Lab, 8 Rue de Rouen, 78440 Porcheville, France.

Classifications MeSH