New advances in stereoselective Meyers’ lactamization. Application to the diastereoselective synthesis of β-substituted oxazoloazepinones

Alexis Bouet 1 Sylvain Oudeyer 1 Georges Dupas 1 Francis Marsais 1 Vincent Levacher 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : A stereoselective approach to the preparation of 7,5-fused bicyclic lactams based on Meyers’ lactamization is presented. The lactamization step is conducted at 0 °C with 6-oxohexanoic acid 1 and with various chiral aminoalcohols in the presence of 2-fluoro-1-ethylpyridinium tetrafluoroborate (FEP) as an activating agent. Under these mild conditions, bicyclic lactams 2–4 were obtained in satisfactory yields and diastereoselectivities up to 95%. To account for the high level of diastereoselection, the mechanistic aspects of Meyers’ lactamization were investigated by means of in situ infrared spectroscopy. Finally, the lactam enolate derived from 2 was subjected to reaction with various electrophiles, furnishing the corresponding β-substituted oxazoloazepinones 5–9 in good yields (up to 86%) and in moderate to excellent diastereoselectivities ranging from 27% to 95% de.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278757
Contributeur : Sylvain Oudeyer <>
Soumis le : mercredi 4 septembre 2019 - 15:45:10
Dernière modification le : mardi 1 octobre 2019 - 11:52:36

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COMUE-NORMANDIE | CNRS | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE

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Alexis Bouet, Sylvain Oudeyer, Georges Dupas, Francis Marsais, Vincent Levacher. New advances in stereoselective Meyers’ lactamization. Application to the diastereoselective synthesis of β-substituted oxazoloazepinones. Tetrahedron: Asymmetry, Elsevier, 2008, 19 (20), pp.2396-2401. ⟨10.1016/j.tetasy.2008.10.014⟩. ⟨hal-02278757⟩

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