title: N-isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines: expeditive asymmetric synthesis of the calcimimetic (+)-NPS R-568.
abstract: An efficient and high-yielding approach for the asymmetric synthesis of calcimimetic (+)-NPS R-568 (1) has been developed. The key step of the synthesis is the highly diastereoselective addition of methyl Grignard to the (SS,E)-N-(3-methoxybenzylidene)-2-propanesulfinamide [5(S)], which afforded a single diastereoisomer in high yield in short reaction time.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, c/ Prof. Garcia Gonzalez, 2, 41012 Sevilla, Spain. inmaff@us.es
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Fernández
authors.forename: Victoria
authors.initials: V
authors.lastname: Valdivia
authors.forename: Noureddine
authors.initials: N
authors.lastname: Khiar
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010627:Phenethylamines; D011437:Propylamines; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis*
chemical_list: D000814:Aniline Compounds; D007097:Imines; C107873:N-(2-chlorophenylpropyl)-1-(3-methoxyphenyl)ethylamine; D010627:Phenethylamines; D011437:Propylamines; D013440:Sulfides