Preparation of β-Lactams by Mannich-Type Addition of Ethyl(trimethyl­silyl)acetate (ETSA) to N-(2-Hydroxyphenyl)aldimine Sodium Salts

Abstract : The synthesis of highly substituted β-lactams was achieved by addition of air-stable ethyl(trimethylsilyl)acetate derivatives to N-(2-hydroxyphenyl)aldimine sodium salts in a THF-EtCN mixture. This reaction proceeds with moderate to good yields and diastereomeric ratio of up to 78:22. The reactivity of the N-(2-hydroxyphenyl)aldimine can be modified by simply changing the co-solvent from EtCN to MeCN to afford the cyanomethylated addition product.
Type de document :
Article dans une revue
Liste complète des métadonnées

https://hal-normandie-univ.archives-ouvertes.fr/hal-02278770
Contributeur : Sylvain Oudeyer <>
Soumis le : mercredi 4 septembre 2019 - 15:52:47
Dernière modification le : mardi 1 octobre 2019 - 11:37:17

Identifiants

Citation

Vincent Gembus, Thomas Poisson, Sylvain Oudeyer, Francis Marsais, Vincent Levacher. Preparation of β-Lactams by Mannich-Type Addition of Ethyl(trimethyl­silyl)acetate (ETSA) to N-(2-Hydroxyphenyl)aldimine Sodium Salts. SYNLETT, Georg Thieme Verlag, 2009, 2009 (15), pp.2437-2440. ⟨10.1055/s-0029-1217729⟩. ⟨hal-02278770⟩

Partager

Métriques

Consultations de la notice

19