Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen: A. Gómez-Palomino, P. Romea, F. Urpí
Synthesis 2018, DOI: 10.1055/s-0037-1609966


Enolates derived from chiral N-acyl-oxazolidin-2-ones have long been considered among the most effective workhorses in organic synthesis, since the pioneering work of Professor David Evans. Recently, the group of Professor Fèlix Urpí from the University of Barcelona (Spain) reported a new application of these versatile chiral auxiliaries for the synthesis of non-racemic α-hydroxy carboxylic acid derivatives and 1,2-diols using a convenient oxidation method.

Professor Urpí said: “A simple and stereocontrolled Cα-oxidation of chiral N-acyl oxazolidinones with environmentally benign molecular oxygen takes advantage of the biradical character of their titanium(IV) enolates, which permits to prepare enantiomerically pure α-hydroxy carboxylic derivatives without the need for any reducing agent.”
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