Verkade's Superbase as an Organocatalyst for the Strecker Reaction

Jian Yang (1) , Bastien Chatelet (1) , Fabio Ziarelli (2) , Véronique Dufaud (3) , Damien Hérault (1) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 AMU SPEC - Spectropôle - Aix Marseille Université
3 C2P2 - Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265

Proazaphosphatranes-Verkade's superbases-proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low catalyst loading and short reaction times were required for the reaction to proceed efficiently. A remarkable initial turnover frequency (TOF), close to 105 h–1, was achieved, associated with an excellent selectivity since no side reactions were observed. A reaction mechanism was proposed and the key role played by the apical nitrogen in the proazaphosphatrane structure was demonstrated.

Domaines: Chimie organique; Catalyse

Jian Yang, Bastien Chatelet, Fabio Ziarelli, Véronique Dufaud, Damien Hérault, et al.. Verkade's Superbase as an Organocatalyst for the Strecker Reaction. European Journal of Organic Chemistry, 2018, 2018 (45), pp.6328-6332. ⟨10.1002/ejoc.201801170⟩. ⟨hal-02079946⟩