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 of the Strecker Synthesis

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:

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.

One-Pot Catalytic Synthesis of α-Tetrasubstituted Amino Acid Derivatives via In Situ Generation of N-Unsubstituted Ketimines
Y. Kondo, Y. Hirazawa, T. Kadota, K. Yamada, K. Morisaki, H. Morimoto, T. Ohshima, Org. Lett., 2022, 24, 6594-6598.

Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature
A. M. Seayad, B. Ramalingam, K. Yushinaga, T. Nagata, C. L. L. Chai, Org. Lett., 2010, 12, 264-267.

Dual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-quinolinolato) Aluminum Complex
J. P. Abell, H. Yamamoto, J. Am. Chem. Soc., 2009, 131, 15118-15119.

Efficient Three-Component Strecker Reaction of Aldehydes/Ketones via NHC-Amidate Palladium(II) Complex Catalysis
J. Jarusiewicz, Y. Choe, K. Soo. Yoo, C. P. Park, K. W. Jung, J. Org. Chem., 2009, 74, 2873-2876.

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.

Synthesis of α-Aminonitriles through Strecker Reaction of N-Tosylaldimines Using Molecular Iodine
B. Das, P. Balasubramanyam, M. Krishnaiah, B. Veerenjaneyulu, G. C. Reddy, Synthesis, 2009, 3467-3471.

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.

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides
Y. Takahashi, R. Yoshii, T. Sato, N. Chida, Org. Lett., 2018, 20, 5705-5708.

One-Pot Three-Component Synthesis of α-Iminonitriles by IBX/TBAB-Mediated Oxidative Strecker Reaction
P. Fontaine, A. Chiaroni, G. Masson, J. Zhu, Org. Lett., 2008, 10, 1509-1512.

Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction
J.-B. Gualtierotti, X. Schumacher, Q. Wang, J. Zhu, Synthesis, 2013, 45, 1380-1386.