Preparation of β-Lactams by Mannich-Type Addition of Ethyl(trimethyl­silyl)acetate (ETSA) to N-(2-Hydroxyphenyl)aldimine Sodium Salts - Normandie Université Accéder directement au contenu
Article Dans Une Revue SYNLETT Année : 2009

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

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-02278770 , version 1 (04-09-2019)

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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, 2009, 2009 (15), pp.2437-2440. ⟨10.1055/s-0029-1217729⟩. ⟨hal-02278770⟩
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