Chiral Bronsted acid catalysts. Activation of methyl 3,3,3-trifluoropyruvate by hydroxymethylpyridine-containing half-sandwich complexes was written by Carmona, Daniel;Lamata, Pilar;Sanchez, Antonio;Pardo, Pilar;Rodriguez, Ricardo;Ramirez, Paola;Lahoz, Fernando J.;Garcia-Orduna, Pilar;Oro, Luis A.. And the article was included in Organometallics in 2014.Computed Properties of C7H9NO This article mentions the following:
The coordinated OH group in cationic 2-hydroxyalkylpyridine (NOH) chiral phosphoramidite (P1-P5) half-sandwich complexes [(ηn-ring)M(NOH)(Solv)][SbF6] and [(ηn-ring)M(PyOH){(R)-P1}][SbF6]2 [(ηn-ring)M = (η5-C5Me5)Rh, (η5-C5Me5)Ir, (η6-p-MeC6H4iPr)Ru; PyOH = hydroxymethylpyridine ligand; (R)-P1 = (R)-1,1′-binaphthyl N,N-dimethylphosphoramidite (R-monophos)] is deprotonated by Na2CO3, rendering bi- or mononuclear compounds [{(ηn-ring)M(μ-O-κ2N,O-PyO)}2][SbF6]2 and [(ηn-ring)M(PyO){(R)-P1}][SbF6], resp. The complexes have been characterized by anal. and spectroscopic means, including the determination of the crystal structures of [{(ηn-ring)M(μ-O-κ2N,O-PyO)}2][SbF6]2 (8a, PyOH = 2-hydroxymethylpyridine, (ηn-ring)M = (η5-C5Me5)Rh; 8c, (ηn-ring)M = (η6-p-MeC6H4iPr)Ru, PyOH = 2-hydroxymethylpyridine) and [(η5-C5Me5)Ir(PyO){(R)-P1}][SbF6] [11b, PyOH = (R)-2-(1-hydroxyethyl)pyridine] by x-ray diffractometric methods. In complexes [(ηn-ring)M(NOH)(P*)][SbF6]2 (P* = P1-P5) the proton of the coordinated hydroxypyridine ligand is able to activate the carbonyl group of Me 3,3,3-trifluoropyruvate toward the Friedel-Crafts addition of indoles. In most cases, quant. conversion is achieved in a few minutes, at -70°, with an ee of up to 82%. NMR data support the activation of the pyruvate by interaction between its carbonyl oxygen and the OH group of the coordinated hydroxymethylpyridine. Therefore, the metallic complexes act as Lewis acid assisted Bronsted acid catalysts. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Computed Properties of C7H9NO).
6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Computed Properties of C7H9NO
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