One‐Pot Synthesis of α‐Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides

• Published in: European journal of organic chemistry Vol. 2021; no. 25; pp. 3634 - 3640
• Main Authors: Yu, Bao, Bodinier, Florent, Saague‐Tenefo, Maximiliene, Gerardo, Patrice, Ardisson, Janick, Lannou, Marie‐Isabelle, Sorin, Geoffroy
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 07.07.2021; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Subjects: Alkylation; Chemical Sciences; Chemistry; Chemistry, Organic; Cyanation; Formamide; Nitriles; Physical Sciences; Reagents; Science & Technology; Strecker reaction; Synthesis; Titanium isopropoxide; α-Amino nitrile; AMINONITRILES; REAGENTS; Cyanation; Titanium isopropoxide; CO2; N-FORMYLATION; alpha-Amino nitrile; TERTIARY; MILD; Formamide; Strecker reaction; REDUCTION; SECONDARY-AMINES; CARBON-DIOXIDE; CATALYSTS
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202100418

In this work, we describe the one‐pot synthesis of α‐amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in scope and the conditions are mild, inexpensive, and easy to set‐up, providing numerous α‐amino nitriles in good yields (34 examples, 41–94 % yield). Easy and straightforward access to α‐amino nitrile units by one‐pot synthesis through a reductive Strecker cyanation from readily available formamides. The reaction is broad in scope and the conditions are mild, inexpensive, and easy to set‐up, providing numerous α‐amino nitriles in good yields (34 examples, 41–94 % yield).