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Synthesis of α-Aminonitriles

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Strecker Synthesis


Recent Literature


RuCl3-catalyzed oxidative cyanation of tertiary amines with sodium cyanide under molecular oxygen at 60°C gives the corresponding α-aminonitriles in excellent yields. This reaction is clean and should be an environmentally benign and useful process.
S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc., 2003, 125, 15312-15313.


A novel, simple and efficient one-pot synthesis of α-aminonitriles has been achieved by a three-component condensation of carbonyl compounds, amines and trimethylsilyl cyanide in the presence of (bromodimethyl)sulfonium bromide as a catalyst at room temperature.
B. Das, R. Ramu, B. Ravikanth, K. Ravinder Reddy, Synthesis, 2006, 1419-1422.


An environmentally benign and highly efficient, biomimetic procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) using β-cyclodextrin as a catalyst and water as solvent afforded α-aminonitriles in quantitative yields. The catalyst can be recycled a number of times without loss in activity.
K. Surendra, N. S. Krishnaveni, A. Mahesh, K. R. Rao, J. Org. Chem., 2006, 71, 2532-2534.


A very fast, simple one-step, environmentally friendly procedure for the synthesis of α-aminonitriles in high yields from aldehydes, using trimethylsilyl cyanide in the absence of solvent, gives almost quantitative yields of the corresponding α-aminonitriles. However, only cyclic ketones afford the corresponding α-aminonitriles in excellent chemical yields.
A. Baeza, C. Nájera, J. M. Sansano, Synthesis, 2007, 1230-1234.


An N-heterocyclic carbene as a nucleophilic organocatalyst allows the cyanation of ketones and ketimines with TMSCN in good yields under mild reaction conditions.
Y. Fukuda, K. Kondo, T. Aoyama, Synthesis, 2006, 2649-2652.


Aryl imines, formed in situ from aldehydes and amines undergo mild nucleophilic addition with trimethylsilyl cyanide on the surface of montmorillonite KSF clay to afford the corresponding α-aminonitriles in excellent yields. The solid acid can be recovered and recycled in subsequent reactions with a gradual decrease of activity.
J. S. Yadav, B. V. S. Reddy, B. Eeshwaraiah, M. Srinivas, Tetrahedron, 2004, 60, 1767-1771.