title: Highly diastereoselective alpha-hydroxylation of Fox chiral auxiliary-based amide enolates with molecular oxygen.
abstract: Using a trifluoromethylated oxazolidine (Fox) chiral auxiliary, the hydroxylation reaction of enolates was very efficiently performed under smooth and friendly conditions with molecular oxygen as oxidizer. This reaction occurred with an extremely high diastereoselectivity. After cleavage, the chiral auxiliary is efficiently recovered and highly valuable enantiopure oxygenated carboxylic acids and alcohols are released.
authors.affiliation: Laboratoire Synthèse Organique Sélective et Chimie bioOrganique (SOSCO), Université de Cergy-Pontoise, 5 Mail Gay-Lussac 95000 Cergy-Pontoise Cedex, France.
authors.forename: Hodney
authors.initials: H
authors.lastname: Lubin
authors.forename: Arnaud
authors.initials: A
authors.lastname: Tessier
authors.forename: Grégory
authors.initials: G
authors.lastname: Chaume
authors.forename: Julien
authors.initials: J
authors.lastname: Pytkowicz
authors.forename: Thierry
authors.initials: T
authors.lastname: Brigaud
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000577:Amides; D002264:Carboxylic Acids; D007659:Ketones; D010080:Oxazoles; C064210:oxazolidine; D010100:Oxygen