Personne : Ollevier, Thierry
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Ollevier
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Thierry
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Université Laval. Département de chimie
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ncf11851616
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Publication Accès libre Asymmetric Diels–Alder reaction of α,β-unsaturated oxazolidin-2-one derivatives catalyzed by a chiral Fe(III)-bipyridine diol complex(ACS Publications, 2018-02-08) Ollevier, Thierry; Carreras, Virginie; Jalba, Angela; Li, MaoAn asymmetric FeIII-bipyridine diol catalyzed Diels–Alder reaction of α,β-unsaturated oxazolidin-2-ones has been developed. Among various FeII/FeIII salts, Fe(ClO4)3·6H2O was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO4)3·6H2O and 2.4 mol % of Bolm’s ligand) afforded high yields (up to 99%) and high enantiomeric excesses (up to 98%) of endo-cycloadducts for the Diels–Alder reaction between cyclopentadiene and substituted acryloyloxazolidin-2-ones. Other noncyclic dienes led to decreased enantioselectivities. A proposed model supports the observed stereoinduction.Publication Accès libre New chiral bis(oxazolinyl) bipyridine ligands and application in the iron catalyzed asymmetric hydrosilylation of ketones(Taras Shevchenko National University of Kyiv., 2015-12-01) Ollevier, Thierry; Levitre, Guillaume; Keipour, Hoda; Jalba, Angela; Lauzon, SamuelC2 symmetrical 6,6'-bis(oxazolinyl)-2,2'-bipyridine (bipybox) chiral ligands have been synthesized from readily available 2,2'-bipyridine. Catalytic asymmetric hydrosilylation of ketones was studied using this family of ligands in the presence of iron(II) acetate.Publication Accès libre Copper-catalyzed carbenoid insertion reactions of a-diazoesters and a-diazoketones into Si–H and S–H bonds(American Chemical Society, 2017-01-28) Ollevier, Thierry; Delage-Laurin, Léo; Keipour, Hoda; Jalba, AngelaAn efficient copper-catalyzed carbenoid insertion reaction of a-diazo carbonyl compounds into Si–H and S–H bonds was developed. A wide range of a-silylesters and a-thioesters was obtained in high yields (up to 98%) from a-diazoesters using 5 mol % of a simple copper(I) salt as catalyst. Using 0.05 mol % of the same catalyst, a-diazoketones led to a-silylketones in low to good yields (up to 70%).Publication Accès libre α-thiocarbonyl synthesis via feᴵᴵ-catalyzed insertion reaction of α-diazocarbonyls into S–H bonds(Royal Society of Chemistry, 2019-02-18) Ollevier, Thierry; Carreras, Virginie; Keipour, Hoda; Tanbouza, Nour; Jalba, AngelaFe(OTf)₂ was used to catalyze the insertion reaction of α-diazocarbonyls into S–H bonds at 40 °C. A wide range of α-thioesters was obtained in yields up to 96% within 24–48 h from their corresponding α-diazoesters. A scope of thiols was used for the unprecedented insertion reaction with an α-diazoketone leading to yields up to 85% of α-thioketones.Publication Accès libre Enantioselective aromatic sulfide oxidation and tandem kinetic resolution using aqueous H2O2 and chiral iron Bis(oxazolinyl)bipyridine catalysts(Wiley-VCH-Verl, 2016-12-27) Ollevier, Thierry; Régnier, Noémie; Jalba, AngelaAn efficient method for the oxidation of aromatic sulfides was developed using aqueous H2O2 catalyzed by in situ-generated chiral Fe/6,6'-bis(oxazolinyl)-2,2'-bipyridine (bipybox) complex. The corresponding sulfoxides were obtained in high enantio-selectivities (up to 98.5:1.5 er) and good yields (up to 61%) when the mono-oxidation of the sulfides was performed in combination with the kinetic resolution of the sulfoxide into the sulfone.