Catalyst-Free Strecker Reaction in Water: A Simple and Efficient Protocol Using Acetone Cyanohydrin as Cyanide Source

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 20-21; pp. 3896 - 3903
• Main Authors: Galletti, Paola, Pori, Matteo, Giacomini, Daria
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.07.2011; WILEY‐VCH Verlag; Wiley
• Subjects: Aldehydes; Amines; Chemistry; Chemistry, Organic; Cyanides; Ketones; Multicomponent reactions; Physical Sciences; Science & Technology; Amines; Ketones; ONE-POT; CYANATION; Cyanides; Aldehydes; DEHYDROGENASE; ALPHA-AMINONITRILES; Multicomponent reactions; TEMPERATURE; BIOLOGY; 3-COMPONENT CONDENSATION; SOLVENT-FREE SYNTHESIS
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201100089

A simple, convenient, and practical method for the synthesis of α‐amino nitriles through a one‐pot, three‐component Strecker reaction of a carbonyl compound, amine, and acetone cyanohydrin in water has been developed. Reactions proceed very efficiently without any catalyst at room temperature with high chemoselectivity and give, in some cases, the expected α‐amino nitrile pure after direct separation from water. The protocol is particularly efficient for both aliphatic and aromatic aldehydes, and cyclic ketones, in combination with primary and secondary amines. An unusual application of the Strecker reaction to 1,2‐diamines to obtain 1,2‐diamino nitriles, and to cyclic secondary amines is reported. An efficient application of acetone cyanohydrin in water for a multicomponent synthesis of α‐amino nitriles is described.