Strecker Synthesis

The Strecker Synthesis is a preparation of α-aminonitriles, which are versatile intermediates for the synthesis of amino acids via hydrolysis of the nitrile.

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Mechanism

The reaction is promoted by acid, and HCN must be supplied or generated in situ from cyanide salts - in the latter case, one equivalent of acid is consumed in the reaction.

The first step is probably the condensation of ammonia with the aldehyde to form an imine:

The cyanide adds as a nucleophile to the imine carbon, generating the α-aminonitrile:

This product may optionally be hydrolysed to the corresponding α-aminoacid:

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Recent Literature

Supramolecular Catalysis of Strecker Reaction in Water under Neutral Conditions in the Presence of β-Cyclodextrin
K. Surendra, N. S. Krishnaveni, A. Mahesh, K. R. Rao, J. Org. Chem., 2006, 71, 2532-2534.

Solvent-Free Synthesis of Racemic α-Aminonitriles
A. Baeza, C. Nájera, J. M. Sansano, Synthesis, 2007, 1230-1234.

Montmorillonite KSF clay catalyzed one-pot synthesis of α-aminonitriles
J. S. Yadav, B. V. S. Reddy, B. Eeshwaraiah, M. Srinivas, Tetrahedron, 2004, 60, 1767-1771.

Strecker Reaction of Aldimines Catalyzed by a Nucleophilic N-Heterocyclic Carbene
Y. Fukuda, Y. Maeda, K. Kondo, T. Aoyama, Synthesis, 2006, 1937-1939.

Catalytic One-Pot, Three-Component Acyl-Strecker Reaction
S. C. Pan, B. List, Synlett, 2007, 318-320.