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