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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
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278770
Contributor : Sylvain Oudeyer <>
Submitted on : Wednesday, September 4, 2019 - 3:52:47 PM
Last modification on : Thursday, July 2, 2020 - 3:30:10 AM

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COMUE-NORMANDIE | CNRS | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN

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

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