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Stereoselective aminoxylation of biradical titanium enolates with TEMPO
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A highly efficient and straightforward aminoxylation of titanium(IV) enolates from (S)-N-acyl-4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-ones with TEMPO has been developed. A wide array of functional groups on the acyl moiety, including alkyl and aryl substituents, olefins, esters, or a-cyclopropyl, as well as a-trifluoromethyl groups, are well tolerated. This transformation can therefore produce the a-aminoxylated adducts in excellent yields with high diastereomeric ratios (d.r.). In turn, parallel additions to the a,b-unsaturated N-acyl counterparts give the corresponding g-adducts with complete regioselectivity in moderate to good yields. Removal of the piperidinyl moiety or the chiral auxiliary converts the resultant adducts into enantiomerically pure a-hydroxy carboxyl derivatives, alcohols, or esters in high yields under mild conditions. Finally, a new mechanistic model based on the biradical character of the titanium(IV) enolates has been proposed.
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GÓMEZ-PALOMINO, A., PELLICENA ZANÓN, Miquel, ROMO FERNÁNDEZ, Juan manuel, SOLÀ, R., ROMEA, Pedro, URPÍ TUBELLA, Fèlix, FONT BARDIA, Ma. mercedes. Stereoselective aminoxylation of biradical titanium enolates with TEMPO. _Chemistry-A European Journal_. 2014. Vol. 20, núm. 32, pàgs. 10153-10159. [consulta: 25 de gener de 2026]. ISSN: 0947-6539. [Disponible a: https://hdl.handle.net/2445/165397]