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Highly Diastereoselective α-Hydroxylation of Fox Chiral Auxiliary-Based Amide Enolates with Molecular Oxygen

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journal contribution
posted on 02.04.2010, 00:00 by Hodney Lubin, Arnaud Tessier, Grégory Chaume, Julien Pytkowicz, Thierry Brigaud
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.