Enantioselective Construction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric Acid-Catalyzed Friedel–Craft Alkylation of Indoles with 5-Substituted Hydroxybutyrolactams - MédiHAL Accéder directement au contenu
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Enantioselective Construction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric Acid-Catalyzed Friedel–Craft Alkylation of Indoles with 5-Substituted Hydroxybutyrolactams

Résumé

The first intermolecular organocatalytic enantioselective addition of indoles to prochiral 5-membered cyclic N-acyliminium ions, generated from 5-hydroxy-,-unsaturated pyrrolidin-2-ones is reported hereinafter. The reaction proceeds smoothly with a range of 5-hydroxy-5-substituted-,-unsaturated pyrrolidin-2-ones and indoles using BINOL-derived phosphoric acid catalyst to afford ,-unsaturated lactams embedding a tetrasubstituted stereogenic center in high yields and enantioselectivities

Dates et versions

hal-03862745 , version 1 (21-11-2022)

Licence

Domaine public

Identifiants

  • HAL Id : hal-03862745 , version 1

Citer

Milane Saidah, Muhammad Idham Darussalam Mardjan, Géraldine Masson, Jean-Luc Parrain, Laurent Commeiras. Enantioselective Construction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric Acid-Catalyzed Friedel–Craft Alkylation of Indoles with 5-Substituted Hydroxybutyrolactams. France. 2022. ⟨hal-03862745⟩
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