title: Asymmetric nucleophilic monofluorobenzylation of carbonyl compounds: synthesis of enantiopure vic-fluorohydrins and α-fluorobenzylketones.
abstract: Asymmetric nucleophilic monofluoroalkylation of a broad range of aldehydes with an α-fluoro-γ-sulfinylbenzyl carbanion takes place with complete control of the facial selectivity at the carbanion and good to high anti-diastereoselectivity to give easily separable mixtures of two optically pure 1,2-fluorohydrin derivatives (up to 24:1 anti/syn). Separation and removal of the p-tolylsulfinyl group with tBuLi provides enantiomerically pure anti-1,2-disubstituted-1,2-fluorohydrins, whereas α-fluorobenzylketones can be obtained by desulfinylation of the mixture followed by pyridinium chlorochromate oxidation (one-pot process).
authors.affiliation: Organic Chemistry Department, Escuela de Ingenierías Industriales, Universidad de Valladolid, Paseo del Cauce, 59, 47011 Valladolid, Spain.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Arroyo
authors.forename: M Ascensión
authors.initials: MA
authors.lastname: Sanz-Tejedor
authors.forename: Alejandro
authors.initials: A
authors.lastname: Parra
authors.forename: José Luis
authors.initials: JL
authors.lastname: García Ruano
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001593:Benzyl Compounds; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D013454:Sulfoxides; D005461:Fluorine