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http://hdl.handle.net/2445/165397
Title: | Stereoselective aminoxylation of biradical titanium enolates with TEMPO |
Author: | Gómez-Palomino, A. Pellicena Zanón, Miquel Romo Fernández, Juan Manuel Solà, R. Romea, Pedro Urpí Tubella, Fèlix Font Bardia, Ma. Mercedes |
Keywords: | Titani Síntesi asimètrica Titanium Asymmetric synthesis |
Issue Date: | Aug-2014 |
Publisher: | Wiley-VCH |
Abstract: | 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. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1002/chem.201402127 |
It is part of: | Chemistry-A European Journal, 2014, vol. 20, num. 32, p. 10153-10159 |
URI: | http://hdl.handle.net/2445/165397 |
Related resource: | https://doi.org/10.1002/chem.201402127 |
ISSN: | 0947-6539 |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
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