title: Ureidopeptide-based Brønsted bases: design, synthesis and application to the catalytic enantioselective synthesis of β-amino nitriles from (arylsulfonyl)acetonitriles.
abstract: The addition of cyanoalkyl moieties to imines is a very attractive method for the preparation of β-amino nitriles. We present a highly efficient organocatalytic methodology for the stereoselective synthesis of β-amino nitriles, in which the key to success is the use of ureidopeptide-based Brønsted base catalysts in combination with (arylsulfonyl)acetonitriles as synthetic equivalents of the acetonitrile anion. The method gives access to a variety of β-amino nitriles with good yields and excellent enantioselectivities, and broadens the stereoselective Mannich-type methodologies available for their synthesis.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián (Spain).
authors.forename: Saioa
authors.initials: S
authors.lastname: Diosdado
authors.forename: Rosa
authors.initials: R
authors.lastname: López
authors.forename: Claudio
authors.initials: C
authors.lastname: Palomo
mesh_terms: D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009570:Nitriles; D009574:Nitro Compounds; D010455:Peptides
keywords: Brønsted bases; nitriles; organocatalysis; peptides; synthetic methods