Tetrahedron letters

Synthesis of α-aminonitriles by self-catalyzed, stoichiometric reaction of primary amines, aldehydes, and trimethylsily cyanide

JP Leblanc, HW Gibson

Index: Leblanc, Jean-Pierre; Gibson, Harry W. Tetrahedron Letters, 1992 , vol. 33, # 42 p. 6295 - 6298

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Citation Number: 47

Abstract

Abstract α-Aminonitriles can be prepared at room temperature in good yield by either the addition of a primary amine to a mixture aldehyde/trimethylsilyl cyanide (TMSCN) or by the addition of an aldehyde to a mixture amine/TMSCN. The reaction proceeds via the initial condensation of a minute amount of aldehyde and amine groups to generate azomethine bonds and water. The latter then acts catalytically to rapidly convert the aldehyde into the ...