title: Memory of chirality of tertiary aromatic amide: application to the asymmetric synthesis of (S)-α-methylDOPA.
abstract: We describe an original asymmetric synthesis of (S)-α-methylDOPA proceeding by the concept of memory of chirality, the only source of chirality being the starting D-alanine. The initial chirality of the amino acid is temporarily transferred to a dynamic axial chirality of a tertiary aromatic amide. The (S)-α-methylDOPA hydrochloride is obtained after four steps with 98% ee.
authors.affiliation: Laboratoire de Chimie des Procédés et Substances Naturelles, Univ Paris-Sud, ICMMO, UMR 8182, CNRS, Bât 410, Orsay F-91405, France.
authors.forename: Thi Thoa
authors.initials: TT
authors.lastname: Mai
authors.forename: Baby
authors.initials: B
authors.lastname: Viswambharan
authors.forename: Didier
authors.initials: D
authors.lastname: Gori
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.forename: Valérie
authors.initials: V
authors.lastname: Alezra
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008750:Methyldopa / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D008750:Methyldopa