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

作者：Gembus Vincent; Poisson Thomas; Oudeyer Sylvain^*; Marsais Francis; Levacher Vincent

来源：Synlett, 2009, 2009(15): 2437-2440.

DOI：10.1055/s-0029-1217729

• imines
• lactams
• silicon
• phenols
• tandem reactions

The synthesis of highly substituted beta-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.

• 出版日期2009-9-16