title: Crystallization-induced dynamic resolution of Fox chiral auxiliary and application to the diastereoselective electrophilic fluorination of amide enolates.
abstract: A highly efficient crystallization-induced dynamic resolution (CIDR) of trans-Fox (fluorinated oxazolidine) chiral auxiliary is reported. This chiral auxiliary was used for highly diastereoselective (>98% de) electrophilic fluorination of amide enolates. After removal of the chiral auxiliary, highly valuable enantiopure α-fluorocarboxylic acids and β-fluoroalcohols are obtained.
authors.affiliation: Laboratoire Synthèse Organique Sélective et Chimie bioOrganique, Université de Cergy-Pontoise, 5 Mail Gay-Lussac, 95000 Cergy-Pontoise cedex, France.
authors.forename: Hodney
authors.initials: H
authors.lastname: Lubin
authors.forename: Christophe
authors.initials: C
authors.lastname: Dupuis
authors.forename: Julien
authors.initials: J
authors.lastname: Pytkowicz
authors.forename: Thierry
authors.initials: T
authors.lastname: Brigaud
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000577:Amides; D010080:Oxazoles; C064210:oxazolidine