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

This manuscript is dedicated to Peter Vollhardt, who launched SYNLETT 25 years ago and since then has continuously served in a number of important editorial capacities.

Abstract

The copper-catalyzed asymmetric α-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).

Key words

nitrosocarbonyl compounds - copper - bisoxazoline - α-hydroxy phosphonic acid - aerobic oxidation

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