BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2020

BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine

Résumé

The asymmetric synthesis of the 3-allyl-3-hydroxyoxindole skeleton was accomplished in yields up to 99%viaa metal-free and enantioselective allylation of isatins (90-96% ee) using BINOL derivatives as catalysts and an optimized allylboronate. This methodology was applied at a gram-scale to the synthesis of the natural product (R)-chimonamidine.
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Dates et versions

hal-02928635 , version 1 (25-11-2020)

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Citer

Julien Braire, Vincent Dorcet, Joëlle Vidal, Claudia Lalli, François Carreaux. BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine. Organic & Biomolecular Chemistry, 2020, 18 (31), pp.6042-6046. ⟨10.1039/d0ob01386b⟩. ⟨hal-02928635⟩
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