Highly diastereoselective alpha-hydroxylation of Fox chiral auxiliary-based amide enolates with molecular oxygen.
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.
Lubin
Hodney
H
Laboratoire Synthèse Organique Sélective et Chimie bioOrganique (SOSCO), Université de Cergy-Pontoise, 5 Mail Gay-Lussac 95000 Cergy-Pontoise Cedex, France.
Tessier
Arnaud
A
Chaume
Grégory
G
Pytkowicz
Julien
J
Brigaud
Thierry
T
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
D000438:Alcohols; D000577:Amides; D002264:Carboxylic Acids; D007659:Ketones; D010080:Oxazoles; C064210:oxazolidine; D010100:Oxygen