53847-36-2Relevant academic research and scientific papers
Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane
Zhou, Qiwen,Meng, Wei,Feng, Xiangqing,Du, Haifeng,Yang, Jing
supporting information, (2019/11/28)
An asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane was successfully realized with chiral phosphoric acid (CPA) as catalyst and water as additive. A variety of optically active secondary alcohols were obtained in good to high yi
Michael additions of highly basic enolates to ortho -quinone methides
Lewis, Robert S.,Garza, Christopher J.,Dang, Ann T.,Pedro, Te Kie A.,Chain, William J.
supporting information, p. 2278 - 2281 (2015/05/13)
A protocol by which ketone or ester enolates and ortho-quinone methides (o-QMs) are generated in situ in a single reaction flask from silylated precursors under the action of anhydrous fluoride is reported. The reaction partners are joined to give a variety of β-(2-hydroxyphenyl)-carbonyl compounds in 32-94% yield in a single laboratory operation. The intermediacy of o-QMs is supported by control experiments utilizing enolate precursors and conventional alkyl halides as competitive alkylating agents and the isolation of 1,5-dicarbonyl products resulting from conjugate additions that do not restore the aromatic system.
Deprotonative metalation of aromatic compounds using mixed lithium-iron combinations
Nagaradja, Elisabeth,Chevallier, Floris,Roisnel, Thierry,Jouikov, Viatcheslav,Mongin, Florence
experimental part, p. 3063 - 3073 (2012/06/01)
The deprotonation of 2-methoxypyridine was attempted using putative (TMP)3FeLi prepared from different iron sources. Using iodine to intercept the metalated 2-methoxypyridine, the best result was obtained from FeBr2 (1 equiv) using THF at room temperature; nevertheless, in addition to the expected iodide, the corresponding 2,2′-dimer was obtained (86% total yield). The origin of the competitive formation of the 2,2′-dimer was not identified but mechanisms were suggested to explain its formation. It was observed that the nature of the electrophile employed to trap the 3-metalated 2-methoxypyridine has a strong impact on this dimer formation, the latter being favored using iodine (35% yield), but also benzophenone (28%), benzoyl chloride (22%), methyl iodide (27%), allyl bromide (15%), benzyl bromide (41%), and tetramethylthiuram disulphide (36%); for this reason, the yields of the expected derivatives were only 51, 15, 62, 0, 5, 18, and 0%, respectively. In contrast, using aldehydes readily led to the expected pyridine alcohols without dimerization (59% yield using 3,4,5-trimethoxybenzaldehyde and 66% yield using pivalaldehyde). 2,6-Dimethoxypyridine (in 68% yield), anisole (47%), 2,4-dimethoxypyrimidine (50% at C5 and 3% at C6), 2-fluoropyridine (64%), and thiophene (49%) were similarly converted into the corresponding alcohols after subsequent trapping with pivalaldehyde. Using iodine to trap the 2-metalated anisole did not lead to dimer formation, and 2-iodoanisole was isolated in 71% yield.
Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand
Diaz-Valenzuela, M. Belen,Phillips, Scott D.,France, Marcia B.,Gunn, Mary E.,Clarke, Matthew L.
supporting information; experimental part, p. 1227 - 1232 (2009/08/10)
A study on the enantioselective hydrogenation of tertiary alkyl ketones catalysed by a novel class of tridentate-Ru complex is reported. In contrast to the extensively studied [RuCl2(diphos)(di-primary amine)] complexes, this new class of hydro
2-ARYLOXYETHYL GLYCINE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORT INHIBITORS
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Page/Page column 109-110, (2010/02/14)
The present invention relates to certain 2-aryloxyethyl glycine derivatives that exhibit activity as inhibitors of the glycine type-1 transporter, to pharmaceutical compositions containing them and to their use in the treatment of neurological and neuropsychiatric disorder.
