2294-74-8Relevant academic research and scientific papers
Synthesis and molecular structure of the 1-phenyl-2-(2-pyridyl)ethanol intermediate obtained from the condensation reaction of 2-picoline and benzaldehyde
Percino, M. Judith,Chapela, Víctor M.,Cerón, Margarita,Soriano-Moro, Guillermo,Castro, M. Eugenia
, p. 3563 - 3572 (2015)
The 1-phenyl-2-(α-pyridyl)ethanol [or 1-phenyl-2-(2-pyridyl)ethanol] compound was obtained from the Knoevenagel condensation reaction between 2-methylpyridine with benzaldehyde without catalyst or solvent. The compound was characterized by IR, 1H-NMR, and by single crystal X-ray diffraction. The X-ray structure clearly revealed that the compound crystallizes in a monoclinic system with centrosymmetric space group, P21/c, with Z′ = 1. The unit cell dimensions are a = 5.2481(3), b = 8.2862(4), c = 23.8498(14) ?, and β = 96.761(5). The crystal structure showed the formation of one intermolecular hydrogen bond O-H···N between the oxygen atom of the O-H and the nitrogen atom of the pyridine group of the adjacent molecule. The crystallography data gave evidence that the intermediate compound is a new stable 1-phenyl-2-(2-pyridyl)ethanol intermediate which presents an interesting relationship between stability and hydrogen bonds formation in the structure for obtaining similar compounds that have been proposed in the literature. Also, it is shown that it is just before the dehydration process which yields the trans double bond of the 1-phenyl-2-(2-pyridyl)ethene.
Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes
Barrios-Rivera, Jonathan,Xu, Yingjian,Clarkson, Guy J.,Wills, Martin
, (2021/12/02)
The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.
Highly efficient asymmetric bioreduction of 1-aryl-2-(azaaryl)ethanones. Chemoenzymatic synthesis of lanicemine
Liz, Ramón,Liardo, Elisa,Rebolledo, Francisca
supporting information, p. 8214 - 8220 (2019/09/19)
Different ketoreductases (KREDs) have been used to promote a highly selective reduction of several 1-aryl-2-(azaaryl)ethanones (azaaryl = pyridinyl, quinolin-2-yl), the corresponding secondary alcohols being obtained with very high yields and enantiomeric excesses (ee > 99%). The absolute configuration of each optically active alcohol has been assigned by means of modified Mosher and Kelly methods, two shielding effects being evaluated: (1) the Mosher phenyl ring effect on the azaaryl protons and (2) the one of the azaaryl ring on the Mosher methoxy group. In addition, the biologically active amine lanicemine has been synthesized from (R)-1-phenyl-2-(pyridin-2-yl)ethanol, thus proving the utility of the secondary alcohols here prepared.
Cu-Catalyzed Enantioselective Boron Addition to N-Heteroaryl-Substituted Alkenes
Wen, Lu,Yue, Zhenting,Zhang, Haiyan,Chong, Qinglei,Meng, Fanke
supporting information, p. 6610 - 6613 (2017/12/26)
Catalytic enantioselective Cu-B(pin) (pin = pinacolato) addition to N-heteroaryl-substituted alkenes followed by protonation promoted by phosphine-Cu complexes is presented. The resulting alkylboron products that contain a N-heteroaryl moiety are afforded in up to 97% yield and 99:1 enantiomeric ratio. The highly versatile C-B(pin) bond can be converted to a range of useful functional groups, delivering a variety of enantiomerically enriched building blocks that are otherwise difficult to access. The utility of this method is further demonstrated by application to a fragment synthesis of biologically active molecule U-75302. Preliminary mechanistic studies revealed that the adjacent N atom of the heterocycles plays a unique role in high reactivity and enantioselectivity.
Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes
Mao, Dan,Hong, Gang,Wu, Shengying,Liu, Xin,Yu, Jianjun,Wang, Limin
, p. 3009 - 3019 (2014/05/20)
Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes have been investigated. Series of azaarene derivatives were afforded by this reaction. 2-(Pyridin-2-yl)ethanols with common substituents were formed through the LiNTf2-promoted aldol reaction for the first time. 2-Alkenylpyridines, exclusively in the form of the E isomers, were synthesized in the presence of LiNTf2 cooperated with H2NTf. In the presence of La(Pfb)3 as catalysis, 2-alkenylquinolines were obtained in high yields through the reactions between 2-methylquinolines and aldehydes under air.
A study on the BF3-directed lithiation of 2-picoline and 2,3-lutidine
Dhau, Jaspreet S.,Singh, Amritpal
, p. 109 - 114 (2013/11/06)
The lithiation of 2-picoline (1a) and 2,3-lutidine (1b) in diethyl ether has been investigated with and without prior complexation with BF3. The reactions of the BF3 adduct of these moieties (2a and 2b) with lithium diisopropylamide (LDA) and subsequent trapping with benzaldehyde or dimethyl disulfide gave products corresponding to exclusive lithiation at the α-methyl carbon. The yields obtained with these reactions were far superior to that obtained with the lithiation of uncomplexed 1a and 1b. The dilithiation of 2a and 2b has also been investigated and a convenient and efficient synthesis of the diiodo derivatives of 1,2-bis(pyridin-2-yl)ethane has been provided.
Kinetic resolution of secondary alcohols using amidine-based catalysts
Li, Ximin,Jiang, Hui,Uffman, Eric W.,Guo, Lei,Zhang, Yuhua,Yang, Xing,Birman, Vladimir B.
experimental part, p. 1722 - 1737 (2012/04/04)
Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.
Catalytic asymmetric Si-O coupling of simple achiral silanes and chiral donor-functionalized alcohols
Weickgenannt, Andreas,Mewald, Marius,Muesmann, Thomas W. T.,Oestreich, Martin
supporting information; experimental part, p. 2223 - 2226 (2010/06/19)
"Chemical Equation Presented" Biomimetic and efficient: Mixed calcium manganese(III) oxides (see structure; Ca green, Mn red, O white) with elemental compositions and structures mimicking the active site of photosystem II were found to be highly active catalysts for the oxidation of water to molecular oxygen. As for PSII, the presence of Ca2+ greatly enhances the catalyst performance in comparison to the related manganeseonly system Mn2O3.
A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues
Boussonniere, Anne,Ranaivondrambola, Tsiresy,Lebreton, Jacques,Mathe-Allainmat, Monique
experimental part, p. 2456 - 2462 (2010/09/04)
Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.
