title: Substrate control in enantioselective and diastereoselective aldol reaction by memory of chirality: a rapid access to enantiopure β-hydroxy quaternary α-amino acids.
abstract: An asymmetric aldol reaction by memory of chirality is reported with a substrate control of stereoselectivity by aldehyde and rationalized. Starting from l-alanine, several diastereopure and enantioenriched β-hydroxy quaternary α-amino acids have been obtained in three steps. The initial chirality of l-alanine is memorized through the dynamic axial chirality of tertiary aromatic amide.
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO-UMR 8182), Univ. Paris-Sud , CNRS, Bât 410, Orsay F-91405 France.
authors.forename: Baby
authors.initials: B
authors.lastname: Viswambharan
authors.forename: Didier
authors.initials: D
authors.lastname: Gori
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.forename: Valérie
authors.initials: V
authors.lastname: Alezra
mesh_terms: D000409:Alanine / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000577:Amides; D000596:Amino Acids; D000409:Alanine