Phenolic Dienes as Highly Selective Dienophiles in Asymmetric Organocatalyzed Three-Component Vinylogous Povarov Reaction - Archive ouverte HAL
Article Dans Une Revue Journal of Organic Chemistry Année : 2024

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

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).

Domaines

Chimie organique
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Dates et versions

hal-04733247 , version 1 (11-10-2024)

Identifiants

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Aurélien Brion, Vittoria Martini, Marine Lombard, Pascal Retailleau, Nicola Della Ca’, et al.. Phenolic Dienes as Highly Selective Dienophiles in Asymmetric Organocatalyzed Three-Component Vinylogous Povarov Reaction. Journal of Organic Chemistry, 2024, 89 (17), pp.12298-12306. ⟨10.1021/acs.joc.4c01239⟩. ⟨hal-04733247⟩
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