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

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

Domains: Chemical Sciences; Organic chemistry

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⟩