Asymmetric Synthesis of Tertiary α-Hydroxy Phosphonic Acid Derivatives under Aerobic Oxidation Conditions.

The copper-catalyzed asymmetric a-hydroxylation of β-ketophosphonates, using in situ generated nitrosocarbonyl compounds as electrophilic source of oxygen, is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. α-Aminoxy-β-ketophosphonates were synthesized in high yields (up to 97% yield) and high enantioselectivities (up to >99% ee). [ABSTRACT FROM AUTHOR]