title: β-Hydroxyamide-based ligands and their use in the enantioselective borane reduction of prochiral ketones.
abstract: Hydroxyamide-based ligands have occupied a considerable place in asymmetric synthesis. Here we report the synthesis of seven β-hydroxyamide-based ligands from the reaction of 2-hydroxynicotinic acid with chiral amino alcohols and test their effect on the enantioselective reduction of aromatic prochiral ketones with borane in tetrahydofuran (THF). They produce the corresponding secondary alcohols with up to 76% enantiomeric excess (ee) and good to excellent yields (86-99%).
authors.affiliation: Chemistry Department, Science Faculty, Dicle University, Diyarbakir, Turkey.
authors.forename: Murat
authors.initials: M
authors.lastname: Azizoglu
authors.forename: Asli
authors.initials: A
authors.lastname: Erdogan
authors.forename: Nevin
authors.initials: N
authors.lastname: Arslan
authors.forename: Yilmaz
authors.initials: Y
authors.lastname: Turgut
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D006877:Hydroxamic Acids / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000577:Amides; D001880:Boranes; D006877:Hydroxamic Acids; D007659:Ketones; D008024:Ligands
keywords: asymmetric borane reduction; hydroxyamide; prochiral ketones