General and stereoselective aminoxylation of biradical titanium(iv) enolates with TEMPO: a detailed study on the effect of the chiral auxiliaryElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR spectra of compounds described in the Experimental section. CCDC 1835692. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8ob01074a

A comprehensive analysis of the influence of the chiral auxiliary on the α-aminoxylation of titanium( iv ) enolates with TEMPO indicated that ( S ) 4- tert -butyl-1-oxazolidine-2-thione is the most appropriate scaffold to provide a single diastereomer in high yields for a variety of substrates, whic...

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Main Authors: Kennington, Stuart C. D, Gómez-Palomino, Alejandro, Salomó, Ernest, Romea, Pedro, Urpí, Fèlix, Font-Bardia, Mercè
Format: Article
Language:English
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Summary:A comprehensive analysis of the influence of the chiral auxiliary on the α-aminoxylation of titanium( iv ) enolates with TEMPO indicated that ( S ) 4- tert -butyl-1-oxazolidine-2-thione is the most appropriate scaffold to provide a single diastereomer in high yields for a variety of substrates, which converts such a radical reaction into a highly chemo- and stereoselective oxidation. Reactions of Ti( iv ) enolates from N -acyl-4- tert -butyl-1,3-oxazolidine-2-thiones with TEMPO afford a single diastereomer of aminoxylated adducts in high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01074a