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

Vincent Gembus; Thomas Poisson; Sylvain Oudeyer; Francis Marsais; Vincent Levacher

doi:10.1055/s-0029-1217729

Article dans une revue

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

Vincent Gembus ¹ Thomas Poisson ¹ Sylvain Oudeyer ¹ Francis Marsais ¹ Vincent Levacher ¹

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Keywords : Imines Lactams Silicon Phenols Tandem reactions

Domaine :

Chimie / Chimie organique

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278770
Contributeur : Sylvain Oudeyer <>
Soumis le : mercredi 4 septembre 2019 - 15:52:47
Dernière modification le : mercredi 15 avril 2020 - 09:06:02

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

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

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