title: Asymmetric synthesis of ethoxydienamines in superbasic medium mediated by chiral sulfinyl group.
abstract: The direct addition of metalated alkoxydiene 2, obtained from α,β-unsaturated acetal 1 through a LIC-KOR-promoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and SN-sulfinyl imines) afforded N-sulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure β-keto amines 7.
authors.affiliation: Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, Via P. Giuria, 7-10125 Torino, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Blangetti
authors.forename: Gianluca
authors.initials: G
authors.lastname: Croce
authors.forename: Annamaria
authors.initials: A
authors.lastname: Deagostino
authors.forename: Eleonora
authors.initials: E
authors.lastname: Mussano
authors.forename: Cristina
authors.initials: C
authors.lastname: Prandi
authors.forename: Paolo
authors.initials: P
authors.lastname: Venturello