174848-93-2Relevant academic research and scientific papers
(S,S)-(+)-pseudoephedrine α-iminoglyoxylamide as a chiral glycine cation equivalent: A modular and flexible approach to enantioenriched α-amino ketones
Ruiz, Nerea,Vicario, Jose L.,Badia, Dolores,Carrillo, Luisa,Alonso, Beatriz
supporting information; experimental part, p. 2613 - 2616 (2009/05/26)
(Chemical Equation Presented) We have studied the ability of an α-imino glyoxylamide derived from (S,S)-(+)-pseudoephedrine as a valuable chiral electrophile for the preparation of α-amino carbonyl compounds. In this context, the addition of Grignard reagents to the azomethine moiety of this chiral electrophile afforded the expected α-amino amide adducts in good yields and diastereoselectivities. Moreover, these adducts have been transformed into enantioenriched α-amino ketones by exploiting the ability of pseudoephedrine amides to undergo selective monoaddition to the carbamoyl group with organolithium reagents.
