Tiemann cyanohydrin amination

What is Tiemann cyanohydrin amination?

In 1880, Tiemann was the first to report a reaction that converts cyanohydrin into α-amino nitrile using alcoholic ammonia. Tiemann cyanohydrin amination is sometimes referred to as the Strecker-Tiemann reaction because it is a reversed process of the Strecker synthesis.

Tiemann cyanohydrin amination - general reaction scheme - Strecker-Tiemann reaction
Tiemann cyanohydrin amination

R = alkyl, aryl (see list of acronyms)

Tiemann also developed a method for directly adding hydrogen cyanide HCN to aldimine to produce aminonitrile, which has been expanded to include ketimine, hydrazones, semicarbazones, and Schiff bases. The resulting amino nitriles can be hydrolyzed to α-amino acids or transformed into hydantoins. Despite this, the preparation of amino nitriles using Tiemann cyanohydrin amination is not as common as with the Strecker synthesis.

The utilization of Tiemann cyanohydrin amination is applied in the synthesis of α-amino nitriles, which can subsequently undergo conversion to yield the corresponding α-amino acids and hydantoins.

References

Tiemann, F. (1880), Ueber aromatische Amidosäuren. [On aromatic amido acids] Ber. Dtsch. Chem. Ges., 13: 381-385. https://doi.org/10.1002/cber.188001301113

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