title: (S,S)-(+)-pseudoephedrine alpha-iminoglyoxylamide as a chiral glycine cation equivalent: a modular and flexible approach to enantioenriched alpha-amino ketones.
abstract: We have studied the ability of an alpha-imino glyoxylamide derived from (S, S)-(+)-pseudoephedrine as a valuable chiral electrophile for the preparation of alpha-amino carbonyl compounds. In this context, the addition of Grignard reagents to the azomethine moiety of this chiral electrophile afforded the expected alpha-amino amide adducts in good yields and diastereoselectivities. Moreover, these adducts have been transformed into enantioenriched alpha-amino ketones by exploiting the ability of pseudoephedrine amides to undergo selective monoaddition to the carbamoyl group with organolithium reagents.
authors.affiliation: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Bilbao, Spain.
authors.forename: Nerea
authors.initials: N
authors.lastname: Ruiz
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
authors.forename: Dolores
authors.initials: D
authors.lastname: Badía
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo
authors.forename: Beatriz
authors.initials: B
authors.lastname: Alonso
mesh_terms: D002384:Catalysis; D005998:Glycine / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D054199:Pseudoephedrine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D009942:Organometallic Compounds; D054199:Pseudoephedrine; D008094:Lithium; D005998:Glycine