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.
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.
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.
An oxidative Strecker reaction of aldehydes, amines, and TMSCN in a biphasic solvent system in the presence of Oxone, TBAB and sodium bicarbonate affords α-iminonitriles in good yields. This three component reaction is applicable to a wide range of aldehydes and amines.
J.-B. Gualtierotti, X. Schumacher, Q. Wang, J. Zhu, Synthesis, 2013, 45, 1380-1386.